


Alphabet Challenge

by campfiresongsong



Category: Pocket Monsters | Pokemon (Anime)
Genre: Multi
Language: English
Status: Completed
Published: 2014-04-05
Updated: 2014-07-27
Packaged: 2018-01-18 00:31:15
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 26
Words: 74,696
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1408342
Author URL: https://archiveofourown.org/users/campfiresongsong/pseuds/campfiresongsong
Summary: <blockquote class="userstuff">
              <p>An alphabet challenge consisting of (mostly) unrelated lemons including a big variety of different couplings.</p>
            </blockquote>





	1. Anxiety

It was 2:00 a.m. yet May still found herself awake on this calm and clear night. The Grand Festival was beginning this upcoming afternoon and she knew that falling asleep was going to be next to impossible. She was so nervous yet she so excited; this was the biggest event in her life! Just moving on past the preliminary round on such a stage would be such a huge accomplishment for her.

She got up out of bed and walked out onto the balcony of their hotel room. Seeing the beautiful city skyline was soothing for her as she tried to push her upcoming contest out of her mind for the moment. She soaked in the view for several minutes before she found herself getting rather tired. She decided it would best to try and get some rest and crawled back into bed. Miraculously, she closed her eyes and sleep immediately overtook her.

XXX

The next 10 hours had gone by in a blur for May. The contest was going to begin in a mere three hours and nerves were starting to set in for the young coordinator. The quartet was trying to decide what to get for lunch, but May didn’t have an appetite. Her stomach was plenty full; full of butterflies that is.

Conversation had been going on in the background, but May hadn’t paid it any attention before she decided to speak up. “You guys can pick a place yourselves. I don’t feel like eating right now.” The other three people in the room shared blank and understanding stares with each other because they knew how she must have been feeling.

“I think I’ll stay back too,” Ash said as he decided to be the first to speak up, “It wouldn’t be right to leave May all alone right now.” Brock nodded in agreement before nudging Max to the door so they could go and find a good place to eat.

As Ash looked sympathetically over to his younger friend, he remembered how he felt before his first match in the Indigo League. It was a very nerve-wrecking and stressful time. Because of his experience with the feeling, he knew what May needed; something to take her mind off of the contest.

“C’mon May, just stop thinking about it. We all know you’ll be great so there is no need for you to get stressed out about it.” He said in an attempt to help ease her mind. “I wish it were that easy.” She responded glumly.

Ash walked over and sat down next to her on the bed. “I think I’ve got an idea of what we can do to help you out.” He said with a look that May had never seen from him. Slightly confused, she looked up at him and asked “What’s that?”

In a swift motion, Ash put his arm around her back and leaned in to bring their lips together. May’s eyes shot open as she was completely caught off guard by Ash’s unexpected move. He knew that this would not at all have been what she was expecting and he was unsure of how she would react. However, he did know that it would change what she was focused on.

May pulled back and gave Ash a stunned look while saying “What are you doing?” “Just go with it,” he said, “Trust me.” May was still extremely unsure about what to do, but this time when Ash pressed his lips against hers, she kissed back. She slowly found herself melting into the kiss as she pushed everything else to the back of her mind.

As the kissing got more passionate, May became more confident in the idea. She opened up her mouth and let Ash do some exploring. For someone who hadn’t ever even had a girlfriend, Ash was a natural. He was extremely smooth and now had May under his spell.

He broke the kiss for a fraction of a second to get May’s shirt over her head and off of her. May then returned the favor to the aspiring Pokémon master. Their fiery kiss continued as May reached her hand down and started to try and undo Ash’s belt. She didn’t take much time and she quickly tugged Ash’s pants to the ground.

While she was doing this, Ash had gripped his hand on May’s butt. He gave it a couple of squeezes before pulling her shorts off so they could join his. The two of them finally broke apart and locked eyes. A smile took over May’s face as she reached for his boxers and ripped them off. Her mouth opened in surprise as she got a look at Ash’s now freed erection. It certainly was bigger than she what she was expecting.

Ash smirked at the impressed girl in front of him. Not wanting to waste any time, he did the honors of lightly pushing May’s mouth up against his beast. She took in a few inches of him and wrapped her tongue all around it. She started bobbing her head up and down, taking a little more every time she went down on him. Ash gave off repeated groans in admiration as the amateur sucked him off.

Ash now took a good look at May’s rack. She had been blessed with hitting puberty early as her D cup breasts were poking their way out of the royal blue bra. He thought the bra had to be a push-up, but as he removed it to start to play around, they stayed up. Ash was amazed that breasts that size could manage could also be so firm!

As he started to fondle her huge boobs, May continued giving him fantastic treatment. She was now taking in a good 6 or 7 inches of him, and it was about all she could manage. She started gagging on his member as it went part of the way down her throat. She cupped his balls as she continued to work her tongue up and down on his shaft.

“Oh fuck, May” Ash let out. He gave both of her breasts a hard squeeze as he tried to hold on from cumming in her mouth. Knowing that would be an extremely difficult task, he brought May’s head up. He groped her tits for one last time before letting go.

Ash laid back on his back and guided May into getting into a cowgirl position on top of him. Once she gave him the nod of approval, he entered inside of her slowly. She bit down on her tongue as she tried to keep from screaming out in pain. She sucked it up quickly though, and gave Ash the green light again.

He entered in about halfway, before retracting most of the way out, and slowly moving back in. He loved the outstanding feeling that he got as her tight pussy walls clamped down onto his hard penis. Ash let her dictate the pace, and she slowly let it increase as she became more comfortable.

“Oh yeah! Oh Yes! Yes! Ohhh yeahh!” May moaned out in pleasure as pace kept its gradual increase. Once the two of them had a little bit of a rhythm going, Ash reached back up and started to play with May’s magnificent melons. He still had no clue how a girl her age could have boobs so big, but he loved it.

“Damn they’re perfect” Ash grumbled out in fascination as he continued to squeeze away on his new found treasures. May smiled as Ash admired her chest. She knew that they were her best features and that they would be marveled at by many. She enjoyed having Ash fondle them, but it was nothing compared to what she was feeling thanks to his manhood.

“AHHH! Ahh! Ahh! Ahhh! AHHH! MHM! MHM! Oh god!” she let in pure pleasure as Ash started entering her fully and stretched her out to the max in the process. ‘He was so big!’ she thought to herself as she enjoyed soaked in every blissful second.

May’s joy was taken to a whole new level as she finally released and had her first ever orgasm. “AHHHHH!” she let out a short and passionate scream to accompany to the powerful climax. Ash paused for a minute as he allowed for the beautiful brunette to collect herself.

Once she had returned back to Earth, Ash got off of the bed and pulled May off as well. He laid her back across a brown desk and had her hips at the edge. He crossed her legs while also setting them over his shoulders. He stayed standing and started to enter her once again.

This new position gave Ash more control and also allowed for deeper penetration. He wasted no time in taking advantage of either of those perks. He thrusted in deeper and with more vigor than before. “AHH! AHHHHH! AHH! OH! OHHHH! OHH YESSS!” May immediately started to squeal in pleasure.

As Ash continued pumping in and out of May, he really admired the wonderful view in front of him. May was a petite girl with a cute face and a nice smile. She had no pimples and had next to no fat. Her stomach was flat, but as already mentioned, her breasts were huge. He loved watching them bounce up and down as he rocked in and out of her.

Wanting to watch them bounce even more, Ash started raising the frequency of his entries. “OHHH! MHMMM! MHM! AHHHH! OHHHH MY GODD YESS!!!” May screamed out as the raven haired boy- wait no; man, kept pleasuring her.

“OH GOD ASH! OH YES! GIVE ME MORE! I NEED IT! HARDER!! DEEPER!!” she begged out. Now that he was given permission, Ash held nothing back. He entered in as far as he could before pulling out, and then sharply entered back in.

“OH MY FUCKING GOD!!! OHHHH!! OHHHHH! AHHH!” May let out deafening screams while Ash penetrated to spots that she didn’t think was possible. He was hitting her g-spot with every thrust, and she just couldn’t get enough of it

Even though he wasn’t as verbal about it, Ash was also in a state of ecstasy. Her pussy was so tight; even he was surprised that he could fit his whole member inside of her. Her walls clamped down on him so well, “Oh hell yeah” he muttered out.

“AHHHH! AHH! OHHHH MY GODD! OHHH YESSS! AHHHHHHHHH!!!!!” May let out an ear-splitting scream as she hit her second climax of the day. As her juices stormed out, May almost lost all sense of reality. She felt so empty yet so complete; it all just felt freaking fantastic.

Her inner walls clamped down even tighter with the expulsion of juices, causing Ash to very nearly lose control of his own cum. He managed to hold in all in though, and pulled himself out of the worn out girl. Knowing that she couldn’t take another round, Ash turned his focus back to May’s perfect pair of breasts.

He positioned his rod in-between them, and let May proceed to pleasure him. Feeling his cock get smothered by her cleavage was a major turn-on for him. It was sort of like a fantasy that he thought would never actually come true.

He could feel his release coming soon as he continued to play around with her tits. He rubbed his member against them while giving his final squeezes to them as well. He finally let out a deep groan as he shot his semen all over May’s face and chest.

The two of them continued panting after the workout that they had just endured. May glanced over at the clock and her eyes widened as she realized that her report time was in a mere 30 minutes. She hurriedly threw clothes back on her and grabbed her poke balls before rushing towards the door.

Before she left, she looked back over at Ash and said “You were right,” as a big smile took over her face. She then flew out the door and presumably toward the contest hall.

A smile also found its way onto Ash’s face as he smugly thought, She acts like that’s a surprise.


	2. Birthday

**Summary for the Chapter:**

> Drew has never enjoyed getting special attention for his birthday, but this time around, he doesn't mind so much.

Drew set down his plate after he’d finished off the pasta that was served to him. “That was great May, thanks for fixing it. I’ll get started on the dishes.”

“No you won’t,” she stated sternly back as she shot out of her seat and to the sink, “you’ll go and relax while I do the dishes.” Drew shrugged her off and started to run some hot water anyway.

“I’m serious!” she said while pushing him away from the stack of dirty dishes, “I’ll do the dishes and when I’m done I’ll give you your present.” she finished with a small smile.

“You didn’t have to get me anything,” he began while gesturing out with his hand, “wasn’t all this enough?” “NO! I had to get you a real present. Now get out of here!” she said, fed up with her boyfriend’s persistence.

Drew finally gave up and left the room. After May and Ash headed their separate ways, May ended up running into Drew along the paths in Johto. The two of them ending up becoming traveling partners, and much to the amazement of many, a couple as well.

The two of them had just finished competing in the Cianwood City contest when May surprised Drew by telling him that she had renting a beach house for the two of them over the weekend. Drew hated having things done for him just because it was his birthday, but there wasn’t much he could do about it.

About a half hour later, May emerged into the living room and plopped down a bag in front of Drew. “Happy Birthday!” she exclaimed. Drew eyed it for a second before saying “A Victoria’s Secret bag?” He peeked inside and gave another confused look, “an empty Victoria’s Secret bag?”

“Come upstairs if you want to see what was in there” said May as she gave him a suggestive wink. She scurried up the stairs and took a left turn into her bedroom. Drew gave the matter some thought, before lifting himself up and following her lead.

Upon entering the bedroom, Drew closed the door behind him. His girlfriend was now lying down on the bed, and she beckoned him over with her finger. She drew circles on his chest with the same finger before questioning him, “You want me to take these off?” in an obvious reference to her everyday clothes.

Drew slowly nodded his head in response. May removed her usual red bandana with haste before she began to unbutton her shirt. She purposefully took plenty of time undoing each one. Once she finally reached the end, she slipped her shirt off revealing her black lace bra.

“Oh my big breasts can barely fit inside this itty-bitty bra” she said teasingly while she rubbed her fingers along Drew’s cheek, making sure to give him a good view of her breasts that were indeed poking out. She then proceeded on down to below her thighs. She continued performing her striptease, grasping the inside of her waistband but refusing to pull them down any.

She repeated a few similar movements before she spoke up again, “You want to take these off for me?” she asked as she crawled on top of him again. For the second time in a span of a couple minutes, the green-haired coordinator gave a small nod. He gripped both sides of her shorts before yanking them downwards and lifting the over her ankles.

As he did this, it uncovered exactly what May had been bought for him. She was wearing some black g-string underwear that matched with her bra. The sides that ran around her waist was about as thick as floss, and there were a pair of skimpy triangles that “covered” her front and back.

Drew’s eyes widened as he got a good look at what laid in front of him. He had no idea how he had managed to hook such a fine looking girl, but he was extremely thankful at this point. Seeing that she was being checked out, May reached underneath her bra and began to play with herself. She gave a few rubs and squeezes to show him what he could have.

She then decided to end his pain, so she unhooked her bra in the back and let it join her accumulating pile of clothes. Drew immediately attacked his new friends with his mouth while letting the other one get worked on from his hand. May gave out a soft moan as Drew began playing with her C-cups.

Drew felt clothes being removed from him but he thought nothing of it because he was so focused on his new toys. He continued to squeeze one while licking and sucking on the other. After a minute or two of that, he switched. He kept this up for several minutes while getting some soft moans from May.

He eventually stopped once he realized that she had managed to completely undress him. May then gave him another saucy look before growling out “I’ve been a bad little girl. I need to be punished.” Once he heard this Drew reached over and ripped off her skimpy underwear.

He pushed May down onto her back as he got his knees. He grasped her ankles, had her bend her knees and also brought up her lower torso off the bed so he could position himself at her entrance. Once he got lined up, he began to fire away.

The two of them had only had sex a couple of times, and each time had been more on the passionate side. Drew intended for this night to be a little bit different. He thrusted in his full length and established a quick pace right off the bat.

“OHHH! Ahh! Ahh!” May squealed out in surprise as she didn’t expect for Drew to be forceful with his entrance. It was what she asked for however, and it felt blissful. Drew continued to pump in and out of her while she consistently gave off shrills.

This angle gave Drew a wonderful view of the smoking hot brunette. She had just about every physical feature a guy looked for. Compelling eyes, a great rack, a slim stomach, long legs; she had the whole package.

He kept admiring her as began to pick the tempo up even more. May had been extremely horny and this new style of sex was satisfying for her. “OH YEAH! OH YES! Go harder! Go Faster! I need a full punishment!”

Drew complied with the screaming girl in front of him, giving her exactly what she wanted. He didn’t exactly know why, but there was something incredibly enjoyable about making her scream like she was. He relished the aggressive role.

“OHHH! OH MY GOD! Here it comes! AHHHHHHHH!” May gave off her loudest scream yet as she also let out her first orgasm of the day. Her juices gushed in a forceful jet; it was the most powerful climax that she had ever given off.

Both of them knew that the night was far from over. Drew got straight up on his knees and he pulled May a little closer while throwing her feet over his shoulders. It wasn’t much different than their previous position, but Drew would be able to penetrate a little bit deeper now.

“You’re not done yet” Drew told a heavily panting May. He pushed himself back inside her following the statement, reaching to depths that hadn’t been previously explored. Drew could no longer withhold from letting out deep groans of pleasure; his cock was getting squeezed tighter than it had ever been.

“Oh hell yeah. Take it. Ughh!” Drew let out moans that were covered up because May was much more vocal about her happiness. “OHHH! KEEP GOING!! AHHHH! OH FUCK ME JUST LIKE THAT!!” she yelled out as Drew pounded her most sensitive spots over and over.

As Drew continued to pound in and out of May, he could sense his clock ticking. He gritted his teeth so he could try to postpone his release as long as possible. Knowing that it wasn’t possible to go on forever, he also started to muster up the last bit of energy he had.

He used this energy to increase both the frequency and power of his thrusts. “OHHH! OHHHH! OHHH YESSS! OHHH! OH MY GOD!!” May was giving off screams with even higher volumes to accompany Drew’s new pace.

“AHHH! AH! AHHH! OH DREW!” May couldn’t stop screaming in joy as she felt the finish coming for both of them. Drew bit his lip as he figured he had less than a minute. He refused to leave any energy left unused so he started to go all out.

“AHHHHHH! AHHHH! AHHH! OHHHHHH!” May let out painfully loud yells as she was now getting hammered. Drew was going harder reaching deeper than he ever had. It was a good thing for them that no one was walking around outside because the noise coming from the bedroom echoed out for quite a distance.

“OH YEAHH!!! THAT’S HOW TO PUNISH A BAD GIRL! OH YES! OHH! OH GOOD GOD!” May closed her eyes in bliss while she was getting absolutely drilled. When she had been planning out this night she hadn’t thought it would get this intense. The sex was greatly exceeding the expectations that she had.

“AHHHH! AHH!! AHHHHH!!!!! OHHH! OH! AHHHHHHHHHHH!!” May gave off her final screams as she gave off a climax even stronger than the one she had earlier. Drew was unable to fend it off anymore, and he fired off his load just moments after May.

Both of their intense orgasms lasted for a good ten or seconds; ten seconds that could only be described as heaven. After Drew finally quit shooting his semen inside of his girlfriend, he pulled out and prayed that the birth control pill was able to do its’ job.

The two of them simply sat panting while they relished the unforgettable scene that they had just gone through. Once May managed to get her breathing back to normal, she curled up next to Drew and said “Happy birthday.” Before pecking him on the cheek and proceeding to fall asleep.

“Best damn present I’ve ever had” Drew commented despite the fact that May was sleeping. Remembering how draining their intercourse was, he decided that it would be best to get some rest himself.

For the first time in weeks, Drew went to sleep with a smile as he replayed the events of the night again in his head.


	3. Curiosity

**Summary for the Chapter:**

> When Misty starts to ask herself about Ash, she can't come up with any definitive answers, so she comes up with a plan to cure her curiosity.

Misty stared at Ash as he sat polishing his latest gym badge. Just the other day he had managed to defeat Erika and earn his Rainbow Badge. Misty shook her head watching him hum horribly off tune to some song while wearing his stupid grin of his.

"Four down and four to go!" exclaimed Ash, his smile still as apparent as ever. Misty said nothing, but continued with her ponderous look. "I can't wait to get to Fuchsia City and earn my Soul Badge!" continued Ash.

"I happen to know the gym leader of Fuchsia City; his name is Koga. He is by no means a pushover Ash, you'll have to train hard before you rush into town and demand a battle." said Brock as he looked up from the stew that he was making the trio for lunch.

"Yeah, yeah," Ash responded as he brushed off his friend's advice "You know that I'll train plenty hard. I always do. But for now, when's lunch going to be ready?" questioned Ash.

Brock chose not answer at first, but rolled his eyes at the young trainer's eagerness. "Soon enough Ash, just try to stay patient."

"My God Ash do you care about anything other than Pokémon and food?" said Misty as she finally decided to enter the conversation.

Ash could think of no retort so instead chose to playfully stick his tongue out at his red headed companion. Misty gave a little snort and another shake of her head.

As Ash went over to talk to Brock (more like pester she thought), Misty drifted off into thought. What did Ash care about? Obviously Pokémon. Whenever he wasn't complaining of an empty stomach or busy filling his stomach with food, his mind was on Pokémon. Whether it be training, discussing battle tactics or re-living his past battles, Ash was always talking about Pokémon. Shouldn't guys Ash's age be concerned about things like sports, music and girls? As Misty asked herself this question in her head, her answer brought forth another strange question.

Was Ash gay?

It seemed silly, but Misty could think of no way to positively answer the question negatively. The only time he had ever seemed to be interested in a girl was when he met Giselle, but Misty couldn't help but think he was simply pretending to be attracted to her because Brock was. It would be a shame if he was gay she thought, he was a pretty attractive guy. A little smile crept on her face as she thought about the day at the beach when she had seen him shirtless. She wasn't going to lie to herself, she had a small crush on him. With her curiosity peaked, she now wanted to figure out a way to find out the answer.

________________________________________

"Man, I sure wish I could cook like you Brock. That was great!" Ash remarked later that night after gobbling down yet another delicious meal put together by the Pokémon breeder.

"Oh that was nothing." responded Brock with a small smile "It sure is getting cold, we should probably build a fire. How about we split up and go get some firewood?"

"Oh I don't really want to go out by myself though," started Misty as a plan slowly started coming to mind "How about Ash and I go out together?"

Brock seemed to sense that something was slightly out of the ordinary, but didn't bring it up. "Alright then, try to get back here as quickly as possible though you guys." Brock instructed before walking off into the woods by himself.

Perfect, Misty thought. Now how exactly was she going to pull this off?

________________________________________

"Way to go Ash, now we're lost!" Even though she seemed to be angry with her idiotic traveling companion, she wasn't really. This situation could be put to her advantage.

"Well you're the one who chose to come out here and follow me in the first place!" retorted Ash, with a small hint of venom in his voice.

"You're right Ash, I did."

Slightly confused at Misty's agreement, Ash paused before muttering, "Yeah… well of course I am."

"Do you want to know why I came out here with you?" Misty questioned as she leaned up against a redwood tree.

"Umm... to get firewood?"

"No. I'm curious about something. Come here."

Ash hesitated, what the heck was going on? She wasn't out here to get firewood, but rather to question him? What did she want? These questions raced through Ash's mind as he slowly trudged over towards Misty.

This wasn't going down quite the way Misty had planned. Then again, she really didn't have a plan. She was improvising everything. During her thoughts and visions on what might go down tonight, she had not seen herself doing what she was about to do. But she didn't think any. She had started letting her body think for her instead. She quickly grabbed Ash by the waist, and pulled his lips into hers.

Ash was too stunned to make any movement. He didn't kiss back, nor did he pull away. Misty didn't let this faze her however; she just kept letting her hormones make her decisions for her. She figured she hadn't struck out yet, so she decided to swing for the fences again. She slowly traced Ash's lips with her tongue before forcing her way inside.

At this point, Ash's thought process finally started to kick in. Misty was kissing him. Misty. The girl who constantly complained and pointed out his faults to him, was now kissing him. It did not matter whether or not he truly liked Misty at this point. His hormones had kicked in too. He quickly started to reciprocate the kiss.

Misty gave out a small moan, both out of relief and pleasure. She enjoyed the spontaneous moment for a while before finally pulling away. Before Ash could even stutter his way into a sentence, Misty put her finger over his lips. She gave a seducing smile before sliding Ash's vest off of him. She followed that by removing his hat and shirt. Then she took her sweet time fumbling with his belt, she wanted to tease the boy a little bit first. Once it was removed, she didn't even bother to ask permission before taking his jeans and boxers off in one quick move.

If Ash was actually thinking at this moment, he might have stopped her. But he couldn't think right now, during this experience that he had never dreamed of experiencing. He just let Misty do whatever she wanted.

Misty didn't quite know what to do; she was as new to this as Ash was. His cock was erect and at least half a foot long. Was that big? Was that small? It seemed big to her anyway. She finally slid her mouth over it, and started to use her tongue.

Ash was in a state of euphoria. Nothing he'd ever felt even come close to what he was feeling at this moment. Misty continued to bob her head up and down on his shaft, bringing multiple soft groans from Ash. This felt too good. It was unbelievable. And he wanted more. He put his hand on the back of Misty's head and pushed.

Misty gagged as she tried to fit his whole member inside her mouth. It was extremely uncomfortable at first, but she figured that you had to practice if you wanted to get comfortable with this. She would occasionally take her mouth off and stroke him a few times before sucking him off some more. She tried licking the tip, and could tell that this too was pleasurable, yet teasing too. Soon, as she started to get the hang of loosening up and using her throat muscles, she could tell it was extremely pleasing Ash.

And as wonderful as it did feel to Ash, he stopped her. He couldn't wait anymore. Misty raised her arms and let him slide her shirt up and over her. She then unclipped her bra, and let her perky nipples out. Her breasts were on the small side, but they fit her body nicely. Ash quickly yanked her shorts off, and her panties followed soon after. Her legs were long and toned dramatically due to all the swimming that she did. As Ash's eyes traveled up her legs, he noticed her hairless clit and her firm butt. She looked pretty sexy.

"This is going to hurt." Ash warned.

"I know, but I'm ready." responded Misty, her tone of voice proving that she was indeed ready.

Ash wasted no time in responding to the green light, and slowly inserted his cock into her pussy and broke through her wall. Misty's mouth stretched into a big O as she tried to keep from screaming right into Ash's ear. The pain was excruciating, and she thought she might cry. Just when it came to the point that it was almost unbearable, the pain started to subside. After a few heavy breaths, she was ready.

"Go ahead." She instructed

Ash went in as far as he could before withdrawing back out, and inserting himself back in slowly. He increased his speed gradually as both their comfort levels started to rise. The faster he went, the greater the feeling. Their timing with each other began to sync up and soon Misty began releasing constant moans.

"Harder," she commanded as she positioned herself so that the tree could provide support for her.

Ash quickly complied. "Don't hold back anything." Misty managed to get out between squeals of enjoyment.

His smile intensified with her latest order, and once again he listened. He rammed her with all the force he could muster up. Misty now knew she was on the verge of her climax. "I'm almost there Ash," Misty warned "AHHHHH! THIS FEELS SO GOOD!" She screamed as she released her juices. It was an incredible feeling, and she wanted to feel it again. "Don't stop now Ash! I want this to last for a while." she commanded.

Ash didn't need to be told however, he had no intentions whatsoever of stopping. His thrusts kept coming, each one seemingly more powerful. "OH OH OH OHHH just like that, just like that, oh YES!" Misty screamed as her rough defloration continued. The bark was pressing into her breasts with each fierce movement that she was making, which only multiplied the bliss. She no longer tried to keep her voice down. She was screaming at the top of her lungs as she hit an orgasm, her second.

"OH GOD ASH, KEEP GOING, PLEASE KEEP GOING! OHH YESSS! PUNISH ME LIKE THE SLUT I AM!"

Ash continued with his torrent pace for as long as he could, but he knew he couldn't last forever. Misty had already released a couple of times and he knew he was getting close. He knew that he only had seconds left, so he made them count. He seemed to get an extra adrenaline kick or something, because he managed to multiply his force to even greater levels. Misty's screams were now so loud that they were inaudible to him in a way.

He didn't want to release inside of her so he quickly pulled out. Misty knew that it was now up to her to finish the job. She quickly grabbed his penis and started stroking it again. She opened up her mouth and swallowed it again, her tongue working wonders. Ash knew that this second blowjob would finish it him in a hurry. "Here it comes, Mist!" he shouted before releasing his full load inside of her mouth.

She initially tried to swallow it all, but there was just so much that she couldn't get it down. She started to pull her head back but Ash put his hand on the back of her head and forced her all the way back down. He wanted for this to end his way. "Swallow." he simply commanded. Misty gagged as she tried to fit his somehow still erect cock and his full load of semen in her throat. After several seconds, she finally managed to swallow it all. Ash released his hand and let her come up.

Misty took some deep breaths, while looking up at Ash. They both didn't quite know what to say. They didn't know what had overcome them in that special moment that they had just shared. Misty decided to break the small awkward silence, "We should get back to camp. Brock's probably worried about us." Ash just nodded his head, they could discuss this later.

________________________________________

After walking around for a few minutes, they managed to find their camp again. Brock was sitting on the ground, by the fire that he had built while his companions were out doing their own thing. "What the heck happened to you guys? What took so long?!" Brock asked to his friends with blank looking faces.

"Umm... well we got lost. Really lost." Misty lied unconvincingly. She could tell that he didn't believe her, as he stared her down trying to get a read on her.

Wanting to get out of this situation, Ash quickly announced that he wanted to go to bed early, and crawled into the tent. Misty inwardly cursed him for leaving her alone with Brock. Once he was out of sight, Brock cracked a smile.

Misty looked at him, obviously confused. "Wh-what are you smiling at?"

"Well you see, I got concerned about you guys after you didn't come back so I went out looking for you. Once I got in about a 200 yard radius, your screaming did the rest." Brock said with a smirk.

Misty's whole face went red as she comprehended what he said. He saw them! Or at least heard them anyway. She was so embarrassed that she couldn't think of anything to say. "..."

Brock let go of a short chuckle before adding, "You know, you still could have gotten some firewood on your way back. That is what you were supposed to be getting you know." Brock enjoyed taking in the girl's uncomfortable look for a few more seconds, before deciding that she had suffered enough. "I'll pretend it never happened. Goodnight." he finished before going over to the tent Ash had entered not too long before.

Misty was still shell-shocked. She would never live this down.

"I really need to control my curiosity..."

**Notes for the Chapter:**

> If you like this, make sure to check out the sequel, Hunger!


	4. Dream

**Summary for the Chapter:**

> Brock has always dreamed about Nurse Joy and Officer Jenny, but can he actually hook up with them?

There had been a break-in at the Pokémon center that Brock and his companions were staying at. Someone (presumably Team Rocket) had stolen some very valuable Pokémon medicine. Officer Jenny was currently on the site and discussing the matter with Nurse Joy.

Brock looked at the ladies in admiration. He racked through his mind, trying to come up with a good pick-up line for the two of them. Which one should he go for? Nurse Joy was so beautiful, but so was Officer Jenny. Did he have to choose?

Finally settling upon the perfect lines, Brock approached the girls. “Nurse Joy, I think I need a paralyze heal!” “Why?” She asked Brock, who was basically a stranger to her. “Because you’re stunning.” Brock finished with a dazzling smile.

Joy blushed a little before stammering out a thank you. He then turned to Jenny and said “And as for you Officer Jenny; you remind me of a Deoxys, because you’re out of this world!” Jenny blushed a little herself and let out a giggle.

“Well you can’t hit on both of us, that’s just not right,” Jenny began “You have to pick one.” Brock thought momentarily about what to do; should he go for Jenny or Joy? Were they just messing with him or were they actually flattered? Either way, it was worth a shot.

“I simply can’t choose between two women as beautiful as you, though!” Jenny gave a laugh before asking the strange man, “What’s your name, cutie?”

“My name is Brock, but if I were a Pokémon I think that I’d be an Erectabuzz.” He replied before shutting both his mouth and eyes in disgust with himself. Why the hell did he have to make a sexual joke? Misty wasn’t here to stop him from picking up a girl, and he ruined his chance by saying something so immature and stupid.

Both Joy and Jenny had shocked faces from hearing what he had said, but to Brock’s surprise, neither seemed to be appalled. Instead, they shared a knowing glance, and Jenny then looked back at Brock. “If that’s true, then why don’t you show us?” She said with a suggestive smile.

Brock found himself speechless after hearing those words. He thought for sure that he’d earned a slap for being so forward, but instead they seemed to be going along with it. He wasn’t able to put together a sentence, but his facial expressions showed his emotions better than words could anyway.

“It’s been a long time since either of us has had sex. I think we’ve both got a lot of pent up sexual tension waiting to get out.” Jenny said as she continued to speak for the two of them.

Brock thought his jaw might hit the floor. Jenny took off her police belt as well as her hat while Nurse Joy removed her hat and her white blouse. “Why don’t we go ahead and start the show, honey?” Jenny asked Joy.

The two of them locked lips and quickly started to make out. Brock must have thought that someone was messing with the thermostat because it was getting extremely hot. The two women’s hands were flying everywhere and removing all clothes possible.

Brock simply had to take off his pants at this point to help ease the pain of his throbbing erection. He undressed himself while Joy and Jenny continued with their French-kissing. Their tongues fought a war while they let out passionate moans to each other.

Before Brock could start to jack off to them, however, they pulled away from each other. Joy had been stripped down to her pink one-piece. The triangle that covered her up front rose up and gave her stomach a little coverage and were protecting her D cups from spilling out.

Jenny was donning a two piece set of blue underwear that matched the color of her police hat. Her huge breasts were also threatening to pop out. Neither of their outfits left much to the imagination, but that was still too much for Brock.

The two girls did the honors for each other, each exposing the other fully. Both were fully shaven and their breast sizes were nearly identical. Not only were they huge, but almost more importantly, they were firm. Age hadn’t had an effect on them yet; there was no sag.

Joy hopped up onto the counter that she normally stood behind at work. She dropped her head off upside-down on one end and left her clit at the other end. Brock got in front of her head and let her mouth cover his member. Jenny positioned herself on the other end and started to eat her out.

Joy took in about half of Brock, wrapping her tongue all round him. Jenny knew exactly what she was doing on the other end, and drew moans that were stifled due to the fact that Joy had her mouth full. Brock closed his eyes as he received a blowjob that he honestly never thought that he would ever get.

Brock decided that this was the perfect and probably only opportunity he had to fill one of his fantasies, so he started to face fuck Nurse Joy. Brock used his hands to move her head in a way that it was in sync with his hips. He would bring her head down while he thrusted forward so he could reach far inside her mouth. Joy gave some good gag-reflex action as Brock continued to ram his cock down her throat.

At the same time, Jenny was making a very horny Joy even more wet with the work of her tongue. She used her fingers to spread Joy more open and stuck her tongue in the opening. Joy and Jenny had done this before and Jenny knew just what to do to please her.

Joy was experiencing such pleasure that she knew that she was on the verge of her climax, but before she released anything, she decided to change things up. She had Brock lay down on his back on the floor. She sat down on his fully elongated erection while also leading Jenny to sit on his face.

Brock started to eat out Jenny while letting Joy ride on his member. The girls were facing each other which allowed for Jenny to lean over and play with Joy. She started to use her tongue again, but this time it was in a new location. She also started to receive the very same treatment that she had just given to her pink-haired friend.

Joy let out a long moan as a wave of fantastic feelings took over her. It had been months, wait no, YEARS, since she had had a man inside her. The feeling was almost new to her since it had been so long, and she planned to make the most of this rare occasion.

Brock was enjoying the moment every bit as much as the sexually deprived girls were. Since Joy hadn’t been penetrated in so long, she was still very tight. She was making it very slow and sensual so that both of them could soak in the feelings. Brock was getting his cock squeezed tight and Joy was getting filled plenty despite Brock’s slight lack in size.

The girls were both letting out some soft moans filled with pleasure. “Ahhhh. Ohhh yess!” They had all forgotten about the robbery that brought them together at this point. This took a higher priority in their minds.

Brock used his tongue to the best of his ability while fully enjoying what he was getting down below. Jenny was now using one hand to stimulate Joy’s pussy even more, and she used the other to give attention to Joy’s mounds. She used some techniques that she hoped would get her partner off soon; she wanted her turn with Brock.

Luckily for her, Joy was once again on the verge of her climax. She was now bouncing at a slightly faster pace, and it was possibly the greatest feeling she’d had in the past few years. “Oh my god! Uhh! AHHH YESS!” She finally orgasmed with Brock still inside of her. Brock, however, managed to withhold his climax.

After letting Nurse Joy regain her sense of reality, Officer Jenny took her spot on top of Brock’s rock hard cock. She, however, laid down and faced the other way. Joy then sat on Brock’s and faced the same direction as Officer Jenny.

Jenny immediately let out a long moan now that she was able to experience the same feelings that Joy had. It had been equally as long for her since she had been entered, so she was just as wonderfully tight. “AH!” she let out in surprise and enjoyment as Joy leaned forward and started to give her a rimjob.

They had never experimented with this, but it felt great for Jenny. She was getting the penetration that she so desperately craved while also having her anus licked out. For Nurse Joy, it wasn’t as disgusting as it might sound to some. It was very different from anything else, but it wasn’t vile.

Brock was able to stay in his heaven. His penis was being tightly squeezed once again, and now he was able to eat out Joy. Not only that, but his chest aligned perfectly with Joy’s so that her fantastic breasts pressed down into him.

Jenny took a slightly faster pace than Joy had; she wanted satisfaction and she wanted it as soon as possible. What she was feeling was far more superior than satisfactory though. The rimjob was something new that felt great, but it simply couldn’t compare to having a man fill her up for the first time in so long.

Joy started to rotate every minute or so; she would move her tongue from one hole to the other. She wanted for her friend to be able to have a powerful climax. She, herself, was having to use a little bit of willpower to keep Brock’s mouth from having her release again.

Brock was still in his state of pure bliss. His two favorite women were giving him the best time of his life. He was now timing his upwards thrusts with Jenny’s bounces. He could tell that she was getting close to finishing because of the sounds she was making.

“OH! Oh my god! YES! It’s been too damn long!” she let out joyfully. She decided that her statement held a lot of truth and it was time to fix it. After a few more pushes, she released her juices with a final yelp. “OHHH HELL YEAH!!”

Brock knew that this night wasn’t going to end until he finally gave out, so he got ready for another round. Officer Jenny put a devious look on her face before walking back to her police belt. She came back with a pair of handcuffs and gave a dirty look to Nurse Joy.

She slapped them onto her, before shoving her into the counter that she had laid on earlier. “You have the right to remain silent. Anything you say can and will be used against you in the court of law.” She said while Brock set up behind the bent over Nurse Joy.

He entered behind the “delinquent” and immediately started to pump in and out. Joy wasn’t exactly sure how she was supposed to remain silent throughout this. Brock didn’t wait too long before picking up the pace. Joy simply couldn’t hold it in anymore; “AHHH!” she let out.

Having stripped everything else off her belt; Officer Jenny knew what she could use it for now. She gave a light whip to Joy, “You have the right to remain silent!” She said in a firm voice. Joy now bit her lip in the hopes that it would help her to cease from making any noise.

Brock now had a smirk on his face and he started to become a little rougher. Each thrust was a little harder than the one preceding it. “OHHH! OH!” Joy had to let out another squeal. Jenny again cracked the whip; this time she hit her twice. “I said you have the right to remain silent!”

Brock was fully enjoying the show in front of him, and decided that he would step it up another notch. He started to go as fast as he could make himself go in an attempt to make Joy scream. Joy was panting heavily, but there was nothing she could do to hold in her yells now.

“AHHHH! OHHH! OHH!” She screamed out. Jenny took no time to bring the whip back out. She started to hit her a little harder, not hard enough to seriously harm her of course, but enough to enforce the law. The whips weren’t enough to silence her anymore though.

“OHHH! MHM! MHM! AHHH!” She continued to scream because of the pounding that she was being disciplined with. Because of her constant screams, Jenny made the whipping continuous as well. She had been placing them on her back, but now moved down to her ass.

This only raised the volume of Nurse Joy’s screams, “OHHH! OHHH! AHHHH! AHHHH!” she screeched out. “You. Have. The. Right. To. Remain. Silent.” Jenny said while whipping Joy once with every word that she said.

Brock just kept pummeling Joy throughout all of this. Joy almost seemed like she was crying at this point, “AHHH! UHHH! MHM! UHH! MHM! MHM!” she didn’t even bother to try and remain mute any longer. Jenny just kept giving her lashes, changing cheeks after every couple.

Joy let a huge orgasm at this point, but Brock just kept pumping away. “OH DEAR GOD! OHHHH!” Joy sunk her face down onto the counter to try and muffle her screams some. Brock was having none of that. He reached for her circular strands of hair tied together in the back and he pulled her back up, forcing her to arch her back in the process.

This allowed for Brock to get even deeper and at this point Nurse Joy’s screams were practically ear-piercing, “AHHHHHHH! AHHHHHHHH! AHHHHHH!” Officer Jenny had whipped both of her cheeks red and she decided it might be best to quit that for now. She instead tied It through the loops in her hair so that she could yank her up if need be.

She also reached for her bouncing breasts and started to play harshly with them. She gave them a few pinches and squeezes while reminding her that, “You have the right to remain silent!” With that statement, she pulled roughly up and yanked Joy’s whole upper body up.

Jenny somehow felt sorry and jealous of her pink-haired friend at the same time. She made sure not to show either of these emotions though. She continued to give harsh squeezes on her boobs while Brock gave her everything he had on the other end.

What he lacked in size, he made up for in skill. He knew how to use what he was given, and he was really giving it to Joy now. She had managed to stay quiet for a few moments, but it was all simply too much. “AHHHHH! I CAN’T DO IT! OHHHHHHH!” She let out in a painfully loud manner.

Jenny now reached back with her bare hands and started to spank the poor lady. “You will remain silent!” She commanded while giving her some rough slaps. This once again got Joy to hush up, but Jenny didn’t care. She slapped her regardless; simply to remind her who was in charge.

She’d already orgasmed twice on the night, but Joy knew that another was coming. “AHHH!” She let out a squeal and put her head back down. Jenny responded by harshly jerking her head back up and slapping her even more.

Joy felt so helpless. He hands were cuffed behind her back and her upper body was being forced into the air. It may have been a little painful, but it was extremely erotic and she was moments away from climaxing.

“OHHHHH! AHHHHH!” Joy had to start screaming again. Jenny slapped her with even more vigor now, “That’s quite enough!” She stated. Brock didn’t let up any; he just kept pounding the innocent girl.

“OHHHHHHHHHHHHH! AHHHHHHHHHHHHHHHH!” Joy let out a final scream as she gave off a monstrous orgasm that made her lose control of her body. Brock and Jenny stopped at this point; their job was done.

Joy felt weak from her amazing climax, but she kept consciousness. “You aren’t done yet.” Jenny told the poor, worn-out Nurse Joy. She shoved Joy’s mouth over Brock’s manhood and said to her, “You have to finish what you started.”

Jenny herself took the pleasure of sucking on Brock’s sack whilst forcing Joy to bob her head up and down Brock’s shaft. He let out long groans in approval as the two girls gave him wonderful oral treatment. He reached behind Joy’s head and joined Jenny in forcing her down.

He forced her to take his full length and wouldn’t let her back up. She wrapped her tongue around him and covered every inch of him that she could. Part of him went down into her throat, and she managed to keep from choking on it.

Brock reverted back to what he did earlier in the night by beginning to face-fuck her again. This time, he had the added pleasure of Jenny sucking his balls. He continued to jab his cock inside of Nurse Joy, forcing his way down her throat.

Unfortunately for Brock, his miracle run was coming to a close. He had no idea how he had kept from releasing from so long, but he was getting extremely close now. He gave a few more quick pumps in and out of Joy’s mouth before pulling out and lifting Jenny’s head as well.

He shot his load all over the two ladies. He showered them as jet after jet of cum flew out of his penis. Once he finally finished releasing his semen, Joy and Jenny were covered in it. It was all over both of the girl’s faces and it dribbled down onto their chests as well.

The girls winked at him simultaneously and Brock made sure to take a mental photograph of the extremely hot image in front of him.

XXX

Brock felt a pillow strike him in the face and he woke up in a jolt. He looked around and quickly gathered that Misty was the culprit. He gave her a look that asked “Why?”

Misty shook her head and said, “You wouldn’t stop talking in your sleep for some reason so I had to wake you up.”

Brock’s eyes widened in realization before mumbling softly, “That was one damn good dream.”


	5. Exuberance

**Summary for the Chapter:**

> Pure exuberance and exhilaration have taken over the lives of Ash and Dawn after an incredible couple of days. What will it lead to?

**Exuberance**

The smoke cleared, revealing a beat-up Pikachu that was miraculously still on its feet and a Dragonite that was out cold on the ground. The crowd exploded into cheers for Ash as he had now moved into the finals of the Sinnoh League. Ash pumped his fist and sprinted to his trusty party to celebrate their huge win.

XXX

The hours proceeding Ash’s epic battle flew by for the Pallet-town native. It was now past midnight and he was back at the hotel that he, Dawn, and Brock were staying at. The three of them had gotten separate rooms because each room only had one bed. There was a knock at the door and Ash assumed that it had to be one of his traveling companions.

He opened the door and found Dawn standing outside with a smile. Ash immediately let her in. “Guess you aren’t ready for bed yet either?” he asked, starting the conversation. “I’m still up for a little more celebration,” Dawn started with a small giggle, “this is all just so exciting!”

Dawn had managed to win the Grand Festival the day before, and now Ash was one round away from winning the Sinnoh League. It was safe to say that this was easily the highest high that either of the two young trainers had experienced before.

“Yeah I know. I don’t think I’ll be able to sleep; I’ve still got so much energy in my system.” Ash replied. He certainly wasn’t lying; this was the first time that he had sat down since his match ended. He had never been this amped up in his life.

The two were just sitting on the end of the bed, enjoying each other’s company despite the silence that had arisen. Dawn didn’t exactly know what came into her head at this point, or why she did what she was about to do.

She leaned over and gave Ash a quick peck on the lips. “Congratulations” she whispered out. Ash froze, he didn’t know how to react. Should he take it at face-value, a simple congrats? Or did it mean a lot more than that?

Without wasting too much time, Ash decided to lean over and give a peck back to her. “Congratulations to you too” he whispered back. Light brown eyes locked with a pair of vibrant blue eyes in the ensuing moments. Their pupils seemed to be able to communicate better than their mouths right now.

Suddenly, their eyes closed and their mouths took over the task of communicating once more. Instead of speaking, however, they did it by enjoying a lengthier connection of the lips. Dawn wrapped her arms around Ash’s neck and deepened the kiss.

After running out of breath, Ash had to pull away. Shocked by his own actions, Ash momentarily froze again. He snapped out of his little trance as Dawn began to speak again. “Why don’t we go ahead and get rid of these clothes?” She asked with a little purr.

Ash managed to give a small nod as he began to wrap his head around the magnitude of this moment. Ash slipped his shirt over his head while Dawn brought his pants to the ground. She got on her knees and looked up with a smile.

Seeing that he wasn’t going to back out, Dawn went ahead and pulled his red boxers down as well. His somewhat aroused member popped free causing Dawn’s eyes to widen. She was by all means a virgin, and she honestly wasn’t positive how to go about this. It was too late to back out now, however, so she brushed off her second guesses and chose to get on with it.

She opened up her mouth and then went down on him. She only took in a couple inches to start; she was only a beginner after all. She whirled her tongue around, trying to give equal attention to every part of him. After gaining some comfort, she began to bob her head up and down.

Ash’s groans told her that she was doing the job right, but the fact that his rod hardened up and extended out some more solidified the fact even further. The more her confidence rose, the more that she tried to take in. She found herself to be able to take in most of him, about six inches, but she gagged if she attempted to go down any further.

She continued to bob her head up and down, all while keeping her tongue in constant movement. Ash continued to groan and grunt her name out as he received his first blowjob. The feeling was so wonderful and so unique; it simply had no comparison. He closed his eyes briefly, just enjoying the unbelievable moment.

He now started to act solely on instinct, albeit that is what he does most of the time anyway. He pushed on the back of Dawn’s head, forcing her to choke on him. The sound of her gagging added an extra enjoyable element. He let her go to breathe for a while, but Dawn got the message.

She went all the way down on her own this time, even though she couldn’t fit it in. She knew that it wouldn’t be long before this would cause Ash to lose control. Confirming her beliefs, Ash began to groan louder and a little more frequently.

Unable to take it anymore, Ash put both his hands behind Dawn’s head and thrusted forward for the first and last time. He orgasmed with his dick still filling her mouth and sticking part of the way down her throat. He immediately retracted in order to give Dawn some air.

She managed to swallow everything that he had shot inside of her. Surprisingly, Ash was still completely erect, and they both knew that this meant there was more action to come. She stood up and walked right over to the naked Ash and whispered huskily into his ear, “You know, I’m not wearing any underwear.”

She was still wearing her cheerleading outfit from earlier, and evidently that was all she had on. Ash looked at her and matched her naughty smile with one of his own. He pushed her onto the bed, and pushed her legs so that they were separated and in the air. He lifted up the bottom flaps of her outfit in order to expose her vagina.

The bed happened to be at such a height that Ash only had to give a slight bend in order to meet her. He stopped right at her entrance and made sure that he did, indeed, have the approval to keep going. “Put it all the way in there! I’m ready!” She said with complete confidence.

Ash entered inside her slowly, and upon reaching her protective barrier, he gave one quick, hard thrust in order to break it down. Dawn picked a pillow up and used it to cover her screams. Why must you endure pain like that before you can have sex? The agonizing pain subsided after a short little while, and Dawn nodded again at Ash, now giving him permission to continue.

He began to push in and out at a very slow pace. The feeling that Ash got when Dawn’s virgin walls gripped down tightly onto him wasn’t surpassed by anything. It put the feelings he got from the blowjob to shame.

“Good god you’re tight.” Ash commented in his state of felicity. He began to inch the pace forward, but he only took baby steps to make sure that they both stayed comfortable. He didn’t want to rush things; there was no reason not to extend these jubilant moments for as long as possible.

Dawn was letting out long, soft moans as Ash penetrated her. She didn’t have anybody to compare him to, but from her experiences trying to fit him in her mouth and now down below, she was pretty sure that he was on the big side. He was certainly a tight fit, heck, in her mind, a perfect fit.

She could feel that he was increasing the pace some, but she really wanted to feel it now. “Go faster! Harder too!” She begged to the hopefully soon-to-be Sinnoh Champion. He said nothing in response but rather let his actions do the talking.

He complied with her, letting the pace swell and giving much harder thrusts. He smiled as he looked down at the bluenette. She was stunning; she looked good enough to be cheer-captain. Fittingly, she was wearing her cheerleading outfit, letting Ash pretend that she was, indeed, a cheerleader. There’s just something about guys that makes them attracted to the thought of screwing a cheerleader.

“OH GOD! Yes! So good!” Dawn was becoming more passionate in her dialogue now. Ash was reaching deep inside her, and stretching out her walls about as far as they could currently go. “Give it to me! Fuck me harder!” She commanded out rather helplessly for a command.

Ash hardly let her finish the sentence before he went in accordance with her. He packed plenty of power into each thrust now, making her scream even more. The sight of the screaming cheerleader was an extremely hot image to Ash, and helped him find more strength.

“OHHH! AHHHH YESSSS! Just like that! AHH!” Dawn squealed out as she crept closer to a climax. Ash seemed to know exactly where her g-spot was because he repeatedly smashed into it with tenacity. She was having a very tough time keeping the noise level down, but she honestly didn’t care too much right now.

“AHHHH! OHH! AHHHHH!” Dawn let off her loudest scream yet as she had her first ever orgasm. Hers’ lasted slightly longer than the one that Ash had earlier. She stayed motionless and panting to make up for everything that had just happened.

“I guess we’re even now, hm?” She asked rhetorically. “Not for long.” Ash replied quickly with a newfound sense of control. He ripped off the clothing that still clung to Dawn got onto the bed with her. He shoved her down onto all fours and positioned himself behind her.

It was basically like doggy-style, only Dawn’s face and forearms were flat on the bed. Her back was pretty heavily arched in order to get to the height that Ash needed it to be at. She felt Ash re-enter her from behind and immediately started to groan some more.

Ash went ahead and picked up right where he had left off. He pumped in and out at a fairly fast pace, with deep, vigorous shoves. He was going to make sure that Dawn wouldn’t be able to ask for anything more this session.

Dawn was already letting out some fairly loud moans, only they were muffled by the sheets this time. Ash liked the sound of her yelping, though, and decided to increase the pace even more. Just as he had hoped and expected, he could hear Dawn raise her volume.

“OHHH! OHH! OH!” He could hear her scream out again and again. She was absolutely loving it. She was unsure how many times that an opportunity like this would present herself; she could only hope that she might have the chance to have a time like this again.

They kept on like this for multiple minutes, and soon they both found themselves on the verge of climaxing again. With both of them being as competitive as they were, they made sure to hold off as long as possible.

Since he knew that the timer was getting close to the end, Ash started to use even more energy so that he could go as fast as he possibly could. He was going to leave it all out there; this was going to finish with an exclamation mark.

“AHHHHH! OH ASH!!! OHH! OHH!! AHH!” Dawn was screaming at her maximum volume, but luckily for Ash’s ears sake the noise was cut in half because she was yelling right into the bed. Possibly because he forgot that they were in a hotel room and there were other people on the floor, Ash pulled on Dawn’s straightened hair so her head would come up.

“OHHHH! OHHH! AHHH! YEAHH! YEAH!! OH YEAH!!” Her shrieks echoed throughout the room. She tried to keep fighting, but in the end, it was a losing battle. There was no way that she would be able to outlast Ash.

“AHHHHHHHHHHHH!!!!!” She gave off one loud, definitively last, yell as she let off her second orgasm. The expelling of her juices and the tightening of her inner walls spawned Ash to finish as well. His semen shot into her pussy, while her juices sprayed over his cock.

Ash pulled out and laid on his back. Dawn flipped onto her back too, and they both laid there, saying nothing. Both of them were thinking the same thing; is there a way that I can go back and live these past few days again?

With all of the magic that the two of them had been a part of in the past 48 hours, it was safe to say that the only word that could come close to describing their happiness would be; exuberant.


	6. First

**Summary for the Chapter:**

> There is just something special about being first...

Ash couldn’t believe his eyes when he walked into his house for the first time in a few months. He had just returned from his attempt at the Unova League and had come home alone, as Iris and Cilan had each gone their own way. He decided that it would be best for him to come back home and think things out for a while before he rushed off into his next journey.

Much to his surprise, not only was his mom sitting in the living room waiting for him, but his childhood best friend, Serena, was as well. They both gave him a smile simultaneously as he paused in his shock. He hadn’t seen her in forever, and part of his brain told him that his eyes were deceiving him; she couldn’t really be there.

He soon accepted that she was there, and finally found it in himself to say hello. Once he did, Serena locked her light blue eyes into the magnificent brown eyes that had enticed her childhood. A big, goofy smile spread over both the united friend’s faces, and they took off for each other at the same moment. They wrapped their arms around each other in a fit of joyous laughter.

XXX

Hours flew by for the trio as they caught up with one another. There were plenty of stories to be shared and laughs to be had. Along with each other’s company, they were able to enjoy a delicious homemade dinner made by Delia. She had prepared quite a banquet in honor of Ash’s return home.

Once everybody had finished eating and the lively conversation slowly started to dwindle down, multiple hours had passed and the time was approaching 8 o’clock. Upon seeing the clock, Delia realized that much more time had gone by than she had thought and that she was running late.

“Oh! I almost forgot about my book club meeting! I’ve got to run sweeties, I’ll be back in a couple hours!” Delia sang out as she grabbed her purse and rushed out of the house. The kids could hear the car door slam from inside and the engine revved up, signaling that Ash’s mother had departed.

The two of them decided to keep on talking, but they moved the conversation back to the living room couch. They visited their childhood again, reliving the stories of the past. There certainly were some unforgettable memories that had been shared; times that had given them a strong bond.

“I’ve really missed you, Serena” Ash said with a small smile, honesty filling the low tone that he had spoken with. She held a special place in his heart that no Misty, May, Dawn or Iris was able to replace. He wasn’t sure of the reason why during his first few journeys, but he felt that he was starting to understand it now.

“I’ve missed you too, Ash. A lot.” Serena responded in a soft voice, filled with truth just like Ash’s. There had been nights when she couldn’t sleep due to her thoughts about him. He had crossed her mind at least once a day since the two of them were separated. She had long since come to terms with the fact that she had a crush on the aspiring Pokémon Master.

For the first time since Ash had entered the house, the room fell quiet. They had steered the conversation down onto a new path, and they were unsure of where to go with it now. Ash bit his lip in uncertainty as Serena looked down rather shyly, avoiding Ash’s eyes on her. Finally, she decided that she needed to say something.

“Ash, what would you say we are?” She began with the silent intention that he not answer immediately. “I mean, we’re best friends, right?” She finished with a question that she assumed was an easy yes. “Of course!” Ash responded, his eyes lighting up once more. He was very sure of that answer, but he was slightly unsure of where this was going.

“Are we more?” Serena asked simply, not wanting to spend too much time beating around the bush. Surprisingly, Ash didn’t seem bewildered by the question. He exhaled, pursed his lips, and begged for his brain to send him the correct words. He thought that he knew the answer, but putting it into words was so difficult for him.

“I think… I- um… you’re different. Special. I mean, I like you in a different way than all my other friends. It’s sorta like how I feel towards my mom, but so different! I-uh… I think I like you. You know, like like you, not just like you, but um- yeah.” He finished his rant full of stumbles with a scratch of his head.

Serena giggled at the struggles of the raven-haired boy sitting next to her. “Well I’m glad you feel that way, because I do too.” She said sweetly as she scooted closer to him. She didn’t want to make him too uncomfortable, but she wanted to make sure that they were on the same page with their feelings for each other.

Seeing that Ash didn’t tense up any as she snuggled up next to him, she progressed to the next step. She leaned her head in and kissed him. Initially, she had planned for it to be a brief peck, but after the sensations that flowed through her body as her lips connected with his, she didn’t break away. As she expected, Ash didn’t immediately respond to her bold move.

Eventually, Ash did react, and his reaction was to kiss her back. The background world fell apart for the lovers as they became enraptured in solely each other. Every sense was brought into pleasure by this. The soothing sound of the fireplace and nothing else to break the peace, the smell of one another; Serena smelled like strawberries to Ash, the feeling of heat and passion racing throughout their bodies, the taste of each other’s sweet lips, and the beautiful visions seen with their closed eyes.

Much to the dismay of both of them, their need for air required that they break the kiss. They locked eyes once again as they opened their eyes back up. Craving more, Serena wrapped her arms around Ash’s neck and began a kiss with even more meaning. This kiss had just as much passion within it, but it had a lot more fire behind it.

Serena opened up her mouth and invited that Ash to poke his tongue inside. He jumped on the opportunity, and opened up the same chance for Serena in the process. After exploring the new territory, the competitive youngsters started to try and win the battle between their tongues. Neither had much luck in that aspect, they mostly stayed even.

The intensity rose with every second that they continued. Eventually, Serena slid her hands up to knock off Ash’s hat, cueing him to do the same to hers. They then pulled their lips away, taking in big gasps of air. Afraid to ask any more questions, Serena used actions instead, and unzipped Ash’s jacket. No resistance was offered, so she went ahead and got rid of his black undershirt as well.

Wanting his turn, Ash stopped her from going any further, and pulled off her skirt. He continued to peel clothes off her until she was topless, just like he was. After removing her magnolia pink bra, her breasts, roughly a B cup, were showing. He gazed at them with admiration; they weren’t perfect, no, of course not, but they passed his eye test.

He softly pressed his hands up against them, he had to be gentle with these delicate objects that were foreign to him. He caressed them slowly, running his hands in small circles. Soon, he used his index finger and traced over the same pathway with them. As he brushed up against her nipples, he couldn’t help but notice that they had become hard.

Serena emitted a few small groans as Ash began to throw in a couple of light squeezes. His curiousness and want for experimentation caused him to bring his mouth down upon them. He sucked, licked and continued to squeeze on them, causing for Serena exhale’s to sound more and more like pleasure filled moans.

Ash used his idle hand to slowly trail down her stomach, before reaching her underwear that was becoming increasingly wet. He teased her slightly, rubbing his fingers over her covered crotch. Despite her attempts to remain calm and normal, Serena started to voice more frequent gasps through her bit lips.

“Enough! Just give it to me already!” She voiced as she became impatient. Ash smirked to himself, but stood up nonetheless and took off all his remaining clothes. As his cock came into view, Serena realized that she wasn’t the only one horny, he was at full mast himself. She estimated that he was about 6 inches in length, nothing huge, but she was actually kind of thankful for that.

She slid her panties off and threw them over by her bra that matched them, but left her long, tight, black socks on. A little unsure of how exactly there were going to do this, Ash hesitated before choosing to lay out on the couch. Serena positioned herself on top of him cowgirl style. She slid down about part way, before she felt her wall block her off from going any further.

“Break it, baby.” She stated with as much false composure as she could muster up. She closed her eyes in advance, but once Ash broke through, they shut even tighter as she winced from the sharp pain. She clamped her jaw down while also clenching onto a nearby pillow; there was a strange desire for her not to make any sounds. She was going to defeat this pain silently.

Once he felt Serena relax and give him a small nod of her head, Ash pushed slowly into her. After he did so, he closed his eyes because of the immense bliss that had overtaken him. Not that he’d spent any amount of time imagining it, but it was a far greater feeling than he could have imagined. He fit inside of her perfectly; a tight, snug fit.

The feelings were even better for Serena, due to the excruciating pain that preceded it. Even though that pain was terrible, it was already worth it. The closest she’d come to this feeling was when she fingered herself that one time, but that majorly paled in comparison to having a penis inside of her.

With this new sexual connection, they were both complete. It was like piecing together the last two pieces of puzzle, and the result was beautiful. This wasn’t a one-night stand, a drunken hookup, or simply physical desires. No, this was, strictly as the word implies, love-making. It had the same electricity, fire and passion of their kissing, but took to a whole new level.

Serena started to slowly grind up and down on Ash’s member. This multiplied the magnificent feelings that pulsed through her blood. She resumed the moans that she had started earlier in the night, though these were louder and represented a far more wonderful feeling. She was so in love with this feeling; she couldn’t get enough of it.

Ash started to buck his hips in sync with Serena. The tempo had begun to quicken a little; Serena’s grinds had started to turn more into bounces. They both found that the quicker they went, the more enjoyable it was. Soon enough, Serena was full out riding on Ash as he gave short pumps into her.

“Ohhhh. Ohhh. Ohh. Oh yeah that’s good!” Serena let out as she continued to bounce up and down on Ash’s dick. She was going fast enough now that her boobs were shaking some. She leaned her head back in ecstasy as she let the feeling flow through her body, filling her with a joy that nothing else could give to her.

Ash was releasing constant deep groans of his own as well. Taking the final step with the girl that he had only recently realized that he was deeply in love with was emotionally satisfying, but the physical joy that came along with it brought pleasures equal to and possibly greater than that. Since she had never been penetrated, she was incredibly tight, and that tightness caused for indescribably good feelings.

“Ahhh. Ahhh. Yess! Mhm! It’s so good!” Serena continued to voice her pleasure as she began to bounce as fast as she could. Both of the lovers could feel their oncoming orgasms beginning to accumulate. Each second was better than the last, but at the same time, each second was another tick on the timer.

“Oh god, Ash! It’s coming soon!” She warned the boy as she knew that this couldn’t go on much longer. She tried to put this thought behind her though, the thought of the end brought a dark cloud over the gorgeous rainbow.

“Oh, Serena! I’m almost there!” Ash echoed her statements moments after she had said them herself. He wanted for them to finish at the same time. He didn’t really know why, but that was the only ending that he wanted.

Seconds later, Serena lost control and let her juices fly out of her. Her climax served as the last straw for Ash as well, and he sent his seed shooting into her. They both started to breathe heavily now that they had finished what was more physical exercise than either of them had thought. After several more seconds, they were able to come back down for Earth, and Serena got off of Ash before snuggling up next to him.

“I always knew that you’d be my first. Other guys have tried, but you’re the only man for me.” She breathed out happily.

“You always have been, and always will be, first.” Ash responded back to his new girlfriend.


	7. Girls

**Summary for the Chapter:**

> Gary always has his way with girls, but will May defy this rule?

Gary could pick up just about any girl that he wanted to. He was blessed with his good looks, and was also equipped with a mouth full of smooth words and phrases that could woo the prettiest women. Because of this, and the fact that he was an excellent Pokémon trainer, girls flocked to him. He even had a group of cheerleaders accompanying him on his quest to become the new Hoenn champion.

He’d slept with each of them before; he even had one amazing night with all of them. He never looked for anything like a serious relationship, which bugged a lot of them, but none of that mattered to him. He was the stereotypical womanizer who didn’t seem to look beyond a girl’s outside appearance. There was one girl, however, that really interested him. Unfortunately for Gary, this girl was traveling with Ash instead of him. He intended to change that.

He had just defeated Ash in an intense battle on the outskirts of Mauville Town. The battle had lasted for at least an hour, and darkness had fallen by the end. Even though Gary wasn’t traveling with Ash and his friends, he decided that he would go to the Pokémon center with them because it was getting late and the Pokémon center was certainly better than camping out.

As usual, Ash and Brock got a room card for the room they were sharing while May got a room of her own. Gary got a room of his own as well; his was down the hall from his frenemies. Gary got back to his room, threw his stuff on the ground, and flopped down onto his bed. He picked up the remote and hit the power button multiple times, trying to get the TV to turn on. After concluding that it was broken, he frustratingly got up and went out to the lobby to watch the TV in there.

He sat down on the couch and half-listened to the news for about thirty minutes before May came out and joined him. His eyes widened in surprise as he realized how lucky he was. He couldn’t have drawn up a better situation to get the girl alone if he had tried. He quickly came up with a plan in his head, and then cleared his throat before going ahead and putting the plan in action.

“What are you doing out here?” He started up the conversation as casual as he could.

“I could ask you the same thing,” She replied, not willing to answer the question simply.

“Well my TV wasn’t working so I came out here. Your turn,” Gary prompted her, unfazed by the fact that she wasn’t seeming to be an easy hook.

“My room doesn’t even have a TV. And I wanted to see the weather for tomorrow,” This time May actually answered the question, clearing the first obstacle in Gary’s plan.

“So what’s it like traveling with Ash?” Gary asked as he sat up from his slouched position, and scooted closer to May as discretely as possible.

“Umm… It’s pretty good,” She answered as she started to full uncomfortable. Gary had never talked with her before this, and she wondered why he decided strike up this conversation.

“Are you and him pretty close?” Gary continued to question her while he continued to inch closer to her, though she had yet to notice that part.

“I guess so…” She said, trailing off as her comfort level still failed to improve.

“Are you guys going out or anything?” Gary asked, now officially moving the conversation down the road he had paved.

“No,” She answered, she had now given up on getting the weather forecast.

“You ever been with a man?” Gary fired off another question immediately after she had answered the last.

“No!” She responded firmly, scooting over as she now noticed how close the two of them were.

“How has a girl with looks like yours never been with a man? He asked undeterred, closing the space that May had just created.

“I don’t know! There’s never been an interested guy I guess… not that I’ve been interested either,” She answered yet another question, and now scooted to the edge of the couch to create space once more.

“Well I’m certainly interested, and I think I could interest you too,” Gary said, revealing his motives behind the “friendly conversation”.

“N-no! I’m sorry… but I just… no,” She said in hopes that he would stop talking and leave her alone.

“C’mon baby. You ought to give me a shot,” He said as he put on hand on her side. He leaned in to the point where he had invaded May’s personal space and she could feel the warmth of his breath on her face.

May looked around in hopes that somebody was in the room or would enter the room and stop this from going any further. Unluckily for her, it was only the two of them. Gary was now rubbing his hand along her sides, and as much as she hated herself for it, she silently enjoyed it. With his experience, Gary was able to read her face and know that he was succeeding. He went in for the kill; he leaned in and kissed her on the lips.

“Why don’t we take this back to your room?” He asked, thinking that he might just have it in the bag at this point.

“N-no… I couldn’t do that...” May rejected his request, but it was an extremely weak request and was not enough to get him to stop. He now kissed her cheek multiple times, getting no resistance from May.

“Fine. Then let’s take it back to my room, sweetie,” He smoothly responded as he trailed his kisses down to her neck.

May said nothing this time, she could deny him no longer. Her teenage hormones were raging now as Gary gave her her first hickey. It felt so warm, so new, and so good. She let out a soft moan, which basically served as a white flag in Gary’s eyes. She had finally given in; he had done it once again. His ego managed to soar even higher upon this realization.

Once Gary had finished his job, a job that would probably be difficult to explain in the morning, he guided May off the couch so he could lead her back to his room. He snuck his hand down onto her butt, feeling her up along the way, as May continued to let Gary control her. She didn’t know why she was letting all this go on, for some reason she blindly trusted him to make her feel good.

He unlocked the door, and closed it right back after they had both entered. He pressed his lips back on top of hers, and let his hands do some moving. He brought one back to her tight butt, and used the other to begin removing clothing from the girl under his spell. He removed her signature bandana, and all of the buttons on her shirt before snaking his hand up her shirt and feeling the two things that truly separated May from most girls her age.

There was plenty of heat in the room now, with most of it being emitted from the kissing being done. May knew that it lacked the true electricity of a loving kiss, but the heat alone felt fantastic. She barely even noticed that her clothes were slowly but surely being removed for her. Eventually, Gary withdrew from the kiss that he had initiated.

He ripped off the shirt that he had unbuttoned, and her bra fell down too as he had managed to unclip it while he was fooling around in there. In order to make her feel a little less bashful, Gary removed his own shirt after this. She didn’t have any reason to be self-conscious he thought, she had a rack that was surely the envy of all the girls her age.

“Oh good god…” he muttered out as his suspicions from seeing her with a shirt turned out to be false. She didn’t stuff her bra as he thought she had; she was perfectly natural. She hadn’t even been wearing a push-up bra; she was simple blessed with large, firm tits. He could have fun with those babies all day, but he’d already gotten what was his fair share of fun with them for the night.

Instead, Gary continued undressing himself, taking off his dark blue jeans. His black briefs that he had underneath didn’t stay in sight of very long, as they were discarded quickly. This action revealed what Gary had self-described, and many girls had seconded, as a beast. His current length would already qualify as big, and he wasn’t even fully erect yet.

Gary put on his often present smirk as May gaped. She had told the truth when she said that she had never been with a man, but she’d watched a few videos that were supposed to have been for adults only, and she’d gotten her hands on toys that actually weren’t meant for kids. She knew that she was going to have trouble fitting him inside of her.

“I think you know what to do with it,” Gary commented as May had started to get over the shock of seeing her first human penis. She did, indeed, know what to do with it thanks to those naughty videos. She opened her mouth and slid it over the front half of his rod. She wasn’t sure what she expected to have tasted, but she was happy to find it to be a nice taste.

She closed her eyes and tried to tell her mouth that she was simply sucking on a lollipop or a popsicle or something like that. She sucked on it, and gave her tongue the most exercise that it had seen by moving it along everywhere that she could reach. Each second proved to provide valuable experience as she improved at a modest rate.

Gary, with all of the different girls that he had slept with, had received many better blowjobs, but for a first-timer, May was performing at a slightly above average level. She began to take in a little bit more of him when she felt that she could do so without choking on it. She dare not even imagine of going all the way down on him. She just worked with what she could at this point in time.

Even though she hadn’t done a job that he would remember down the road, she still accomplished the goal that he had silently set for her. His cock was now popping out its full length, extending almost 10 inches from the rest of his body. He eyed May’s shorts, and she got the message right off. She slid her biker shorts off, and her red panties followed them to the pile of clothes that had accumulated.

May lied down across the bed, and Gary crawled in behind her. Without bothering to ask, he slowly inserted himself, waiting for her hymen to stop him at any time. Much to his surprise, it never happened, as unbeknownst to him, it was already broken. Being presumptuous, Gary immediately assumed that she had been lying earlier.

“I thought you said you hadn’t been with a guy,” He said in a questioningly manner.

“I hadn’t! Not until now anyways… but I’ve done some other things,” She said as she let Ash’s rival in on her dirty little secret.

“Well aren’t you a naughty little girl,” Gary said as another smirk came onto his face.

He then began to slowly pump partially in and out of the amateur. He wasn’t going to go all in on the poor girl; no he wasn’t that much of a jerk. Ok, maybe he was, but he wanted to be as nice as he could to May. He didn’t want this to be a one night stand or anything; he wanted to sleep with this beauty as many times as he could. He didn’t want an actual relationship of course, but she had all the assets that he could want in a sexual partner.

May let out some long, soft moans as she lost her virginity while Gary was also unable stay silent due to the pleasure of entering into a girl so tight. He’d had the pleasure of popping the cherry for many different women, and the experience never got old. He didn’t understand why any guy would want to be with an overused, loose girl, because this felt amazing.

Once he thought that he had given her sufficient time, Gary began to penetrate in just a little bit deeper, now over half of his length, as he wanted to explore the depths of her vaginal canals. It seemed that the further in he went, the tighter and more fantastic it felt for him. He hoped that May was getting the same utter enjoyment out of this as he was, and by the sounds of her moaning, he assumed that she was.

“Oh it feels so good!” She let out softly in the midst of her pleasure. When she first discovered the “art” of masturbation, she thought that it felt really good, but actual sex was on a totally different level. Gary’s meat barely even fit inside of her, and caused for her insides to be stretched to levels that they had yet to stretch to.

Every couple of minutes, Gary would add in another inch or so, multiplying the joy for each of them every time that he did so. Though he tried to keep them in, Gary had to give off grunts as his cock was squeezed as tightly as it had ever been. He had also been increasing the very slow pace, but he still kept it fairly slow.

“Oh you’re so big! Oh! Ahh! I think I’m going to cum!” She announced as she tried to hold in her climax for as long as she could. Gary didn’t really heed any mind to what she had said, he only thought of what she would say if he actually put all of himself inside her. He stayed patient though, for he wanted there to be a sequel to this sometime in the future.

“AHHHH!” May let out her first real scream of the night as she orgasmed. It was much more powerful than any of the finishes that she had gotten when she was by herself. After getting over the thrill of how wonderful it felt, she realized that Gary had managed to hold it in, and that meant that they weren’t done just yet.

May returned back to her knees in hopes that she could give Gary the same finish that she had gotten. She picked up right where she left off, remembering the lessons that she had taught herself earlier that same night. She still could only fit in about three-quarters of him, but she hoped that maybe by next time she would a find a way to fit all of him inside her mouth.

Gary, on the other hand, was no longer satisfied with what he was getting. He decided that it was time for him to take control. He grabbed the back of May’s head and forced her to go all the way down to the very base of his cock. He could hear her gagging because of the unexpected move. She thought for sure that she was going to choke if he kept her like this.

Much to her relief, Gary released and allowed her to come back up and get some air. He only gave her a couple of seconds, however, before forcing her back down. She wasn’t ready for this one either, and started choking again, although she probably would have choked regardless of if she was ready or not.

Gary repeated the procedure, and started to quicken it as well. Surprisingly, despite all of his times with women, he had never skull-fucked any of them. He didn’t even know what had given him the idea to do it, but he was glad that he came up with it. May continued to gag as his huge dick continued to force its way down her unready throat.

May didn’t understand how girls learned to breathe like this. Her whole mouth was stuffed full and Gary’s cock went down and seemed to block her air passageways in her throat because of its extensive length. He would pull out momentarily, just long enough for her to take a tiny breath, before pushing his way back down.

“You like that, don’t you, you little slut?” Gary said in a jesting manner. May wasn’t sure how long she would be able to stay conscious if her breathing continued to be cut short like it was now, but she just hoped to tough it out until Gary finished with her. She wouldn’t have to wait too much longer, Gary knew he couldn’t hold it in for very long.

Knowing that he had only seconds left, he got a little rougher with her. He pumped in a few more times, pushing in as far as he could. Finally, when May was probably a good minute or two from fainting, Gary reached his climax. He released his seed with his cock still lodged in her throat. She was forced to swallow it; it didn’t taste that bad though, so she didn’t care.

Gary then took his hands off of May’s head and pulled out of her mouth. She coughed multiple times, and took as many deep breaths as she could. They stayed silent while May tried to return her breathing back to normal. Once she finally had, she began to redress herself. Before leaving, she felt the need to ask Gary something.

“So am I just another hot girl for you to sleep with for one fun night?” She asked in a way that it was more of a statement.

“Of course not,” He responded coolly, in hopes that she wouldn’t hate him. She arched her eyebrows, before escorting herself to the door. When she reached to turn the doorknob, Gary called out to her for one final time.

“Oh, by the way, it’s supposed to rain tomorrow,”


	8. Handyman

**Summary for the Chapter:**

> At their first meeting, Tracy and May hit it off well. Really well.

Ash and his friends had just wrapped up their adventure in Hoenn and decided to travel back home to Ash’s home in Kanto. After visiting with his mom and taking a little bit of a vacation, Ash heard about the Battle Frontier and knew that it was for him. He decided that that would be his next challenge, and his friends decided to keep traveling with him for the time being.

Before they departed to find the first Frontier Brain, Ash wanted to stop in at Professor Oak’s lab so he could see some of his old Pokémon. When they knocked on the door, Professor Oak didn’t answer, but Ash’s old traveling partner, Tracey, did. Tracey was now working alongside Professor Oak as his assistant. Ash introduced his new friends, May and Max, and they started talking about everything that had gone on since Tracey had stayed behind at the lab.

After he remembered why he had come there in the first place, Ash went out into the field so he could find Professor Oak and all his old Pokémon. Max, very excited at the thought of seeing more new Pokémon, went out with him. Brock, who was closer with Oak than he was Tracey, went out with the other boys.

Tracey and May continued the conversation on their, finding out that they had quite a bit in common. Needless to say, a connection was made, and they really hit it off. Tracey ended up offering a tour of the lab to his new friend, who eagerly accepted. He showed her some of the not top-secret research that had been going on, and introduced her to some Pokémon that she had yet to see.

The last room that they entered was a room that was fairly empty. It had a big window overlooking the gorgeous fields full of the lab’s Pokémon, and other than that, it simply had a stool and a bunch of paintings. The paintings were all of different Pokémon, and May thought that whoever made them must have been extremely talented.

“Did Professor Oak buy these?” She asked in her curiosity.

“No, I made all these. I know they aren’t great or anything, but art is my passion,” Tracey answered honestly.

“Are you kidding me? These are fantastic! You have a ton of talent,” She gushed heavy praise out.

“Gee, thanks!” Tracey muttered out, slightly nervous as his face turned to a light scarlet red shade. May started to go up to each individual painting, wanting a zoomed in look at all of them. Tracey walked up behind her as she spent an extended period time in front of one particular painting. He brushed his arm up against her shoulder as he pointed to the different Pokémon in the picture, giving her the names to the ones what she probably hadn’t come into contact with yet.

May turned around to respond to him, but shut her mouth once she realized just how close that they were. Tracey hadn’t intended to get in her personal space, but he now realized the very close proximity of their faces. Neither of them moved for multiple seconds; reading the other’s face and staring into each other’s eyes. Something clicked for them simultaneously, and they closed the short distance between them.

The two of them were exposed to some foreign feeling as their lips connected. Tracey, who didn’t consider himself a smooth guy, was shocked at his own boldness. He asked himself in his head if he had actually just done what he had done, and if this was real, before coming to the conclusion that he didn’t care. May didn’t question the reality of the situation, but she was in disbelief as well. However, she took the some mentality the Tracey had; just enjoy it.

Messages seemed to be communicated through the electricity that was sparked by their kissing. The messages being sent were those of hunger, so Tracey pushed the action forward. He brought his right hand down and brought it back up underneath May’s red shirt. He started to pull up on it, and soon got some assistance from May. They parted their lips very briefly as they slipped her shirt over her head and flung it carelessly.

Seconds later, May copied Tracey’s actions, and they parted once more so that they could remove his shirt as well. May started to poke around at Tracey’s belt, doing her best to get it off. Tracey dedicated himself to a simpler task, and reached back to unclip May’s lime green bra off. He discarded it and began to fondle her. As he continued to play with her, he wondered to himself if she was still developing, because it was hard to believe that she would develop too much more

After a minute or two of struggling, May managed to complete her job, and consequently, she dropped Tracey’s baggy shorts onto the ground. She could feel his throbbing member was being confined inside his constricting underwear, so she tugged once more, causing for Tracey to become completely nude, minus his shoes. She then started rubbing her hand over his crotch; taking her own turn to play around.

Eventually, they separated from each other’s lips for good. Tracey gave a disapproving look as he saw that clothes remained on May; that wasn’t going to work. May knew exactly what he wanted, and she began to remove her shorts. She turned around and bent over in the process; purposely giving Tracey a wonderful view of her cute butt. She jiggled around just a little bit, trying to arouse Tracey even further. It worked perfectly; his eyes bugged out when he was that her back was just as nice as her front.

She gave an almost arrogant smile; she wasn’t actually arrogant, but she wasn’t modest when it came to appearance. She knew she was hot. She wiggled her way out of her skimpy green panties, taking more time than what was actually necessary. After she took her sweet time bring them down to her ankles, she kicked them off, causing them to fly across the room to join the rest of her clothes.

“What do you want do to me?” She asked in a seductive tone, pressing against her own breasts, “What do you want to do with this?” She questioned again as she rubbed her hand up and down the length of his hardened cock. She got down onto her knees and licked her tongue across his shaft. She ran it over his length a couple of times, but before she covered it with her mouth, Tracy decided that he wanted something else.

He leaned May back, spread his legs, and pressed his dick in-between May’s melons. He slowly rubbed it up and down on her chest. She picked up on what was going on quickly, and pressed her tits against his cock. Since her boobs were safely on the large side, she had enough to completely smother him in her breasts. Tracey was grunting heavily he kept pushing his erection up against her fantastic titties.

As previously stated, Tracey wasn’t too great with girls, so he was in still in awe of the situation. It was like he had gotten the hottest, most sought-after girl in school, and was getting to do whatever he pleased with her. He wasn’t sure what was so attractive about boobs, I mean weren’t they just balls of fat? But either way, looking down at his cock snuggled up inside of those treasures nearly made him bust a nut.

He was, in fact, getting close to doing just so, so he reluctantly retracted from his paradise, and inserted himself into May’s mouth. She didn’t waste any time, she immediately began bobbing her head up and down while using her tongue to pleasure Tracey all around. Tracey wasn’t exactly big, but he wasn’t small either. Since he was only average in his length, May was able to engulf all of him.

She would barely even gag when the tip of his cock would find itself at the back of her throat. She could take him in comfortably, which allowed for her to focus entirely on the work of her tongue. This was plenty enough to finish the inevitable that Tracey was postponing for as long as he could. He’d never had a blowjob, much less been deep throated, and found himself unable to keep his cum in any longer.

He shot his hot load down her throat, and she swallowed it without as much as a blink of the eye. She smiled inwardly, proud of the work that she had just done. Tracey pulled himself out of her mouth, and much to the relief of both of them, he was still erect and ready for more. Tracey silently thanked god, he would have been extremely embarrassed if they had to stop after that.

“Mhm that was tasty. But my little pussy is hungry for your cum too,” May growled out, ready for her wet pussy to finally get its fill.

“This might hurt…” Tracey said weakly.

“Oh you’re not my first. A girl like me doesn’t stay a virgin very long you know,” She said, again not afraid to reference the fact that she was a wonderful piece of eye candy. She didn’t mean to come off as a slut; she really wasn’t one, but she’d been penetrated twice before.

Tracey nodded silently; it didn’t bother him that she had already slept with someone else, it was just a little bit surprising. She was right though, she could probably seduce any straight man that she wanted to. He proceeded to push her into bending over his stool, the lone piece of furniture in the room, and positioning himself behind her.

For the who-knows-how-manyth-time of the day, Tracey’s eyes bulged out in a happy surprise. Even if this wasn’t her first time, May was still plenty tight, and it felt like heaven down there. He pushed in further, all the way in, and marveled at how the wonderful feelings grew exponentially. He pulled most of the way out and reinserted himself, still attaining the same level of amazement the second time around.

He repeated his motions a couple more times, before he started to complete the process a little bit faster. Just like anything one does for the first time, Tracey was able to do it faster the more comfortable he became with the foreign process. Before long, he had established a bit of a rhythm at a modest pace. At the time, he was moaning even louder than May was.

Tracey didn’t like that this was the case, and so he started to go just a little bit faster and he began thrusting just a little bit harder. As he expected, May raised her volume a little bit in correlation with his adjustments. This made him happier; therefore, he did the same thing again. He started to go balls-deep with rough thrusts.

“Oh yeah! That’s it! FUCK! OH! Fuck me harder! Oh god, faster! YES!” May was now bellowing out screams that would have been heard if there was anyone else in the lab.

Tracey was happy to comply with the brunette’s wishes. Before he did, however, a thought came to him. Smiling mischievously, he retracted from May, earning a disapproving huff, but put himself back in quickly. This time however, he was entering inside her butt. He could barely get his cock inside of her dainty, tight ass, but he made it fit.

“OH SHIT! Oh it’s so big! I’ve never done anal… oh make me scream,” She pleaded, knowing very well that she would get what she was asking for.

Tracey’s cock was getting clamped on even tighter than before, it was like a Pokémon was using vice grip on him or something. He picked up where he had left off though, giving her rough thrusts that were sure to get her squealing. He pushed in as deep as he could, surprised at how far he was able to get to. Pumping away, Tracey finally felt a small sense of control over the situation for the first time since they began.

“YES! Oh yes! Oh god!” May resumed the screams that had gone on a brief hiatus. She loved the novelty of what they were doing; she was always up for something new. Especially if that something happened to be as pleasing as this was. Her breasts would have bouncing had they not been pressing into the wooden stool that she was bending over.

“OH FUCK!” May didn’t announce that she had climaxed, and Tracey had no way of knowing so, but he thought that she might have. He hoped that it was that way, because he was about to finish, and he didn’t want to leave her hanging. He brought his thrusts up to an even faster speed, and a roughness that he had yet to attain.

May’s yells seemed to be in the background because of the fact that Tracey was focused strongly on what he was doing. He gave her a loud slap on the ass at the same time that he entered in as far as he could for the final time. He released his seed deep inside of her anus, letting out a final grunt of his own. He was disappointed that he had finished earlier than he had hoped, but he was still happy because of how great the experience was.

May stood up and was about to say something, when they both heard voices becoming louder, and the opening and closing of the back door. They put on their clothes in a panic, they had forgotten about the boys that were out in the field. Thankfully, they managed to get dressed before the rest of the group managed to track them down.

A mere 15 seconds after they finished removing any evidence, the four guys poked their heads in the room, ending their search of the two that had stayed behind.

“You guys missed out on a great time!” Max started, before rambling on about all they had done to five pairs of inattentive ears.

“Oh we had a great time in here too. Trust me,” May responded, who was simply glad that her great time went unnoticed by her traveling buddies.


	9. Incarceration

**Summary for the Chapter:**

> When Jessie and James are imprisoned, how will they handle it?

**Notes for the Chapter:**

> WARNING!! This chapter contains rape! No children please!

“Oh I can’t believe that BITCH!” Jessie exclaimed in her rage, “How dare she arrest us? We’ll show her why you don’t mess with Team Rocket! Oh yes we will get revenge!” She continued with her rant inside of a prison cell that she was sharing with James, her partner in crime. Meowth had managed to escape the scene without the cops finding him, but his partners weren’t so lucky.

James did not rant as much as his bossy companion, but he shared her indignation. He could not stand being locked up in a cell, especially since he had done nothing wrong. They were simply doing yard work for a poor old man who could not do it himself. Granted, they weren’t doing it just to help the old man, but he was happy to pay them for the work and they needed the money.

Then, out of nowhere, Officer Jenny came charging down the street and arrested both Jessie and James. When they demanded to know what charges were being pressed against them, she told them that wearing the Team Rocket uniform warranted an arrest. Minutes later, they were thrown inside a small, three bunk bed jail cell, and they were told that their sentence was for five years!

“Five years in here, my ass!” Jessie continued to fulminate over the whole ordeal, “I won’t spend another night in this damn cell!” Her temper had not gone down in the days that she had been locked up. In fact, James wondered if she would ever calm down. He began to fret over five years of putting up with that, but reassured himself that they wouldn’t actually be stuck in there for that long.

“At least they forgot to search us,” James said, hoping to bring a little bit of optimism into the room. Jessie turned to explode on him, but her face softened before any words came out, and instead of yelling, she nodded in agreement. At this point, it was best for them to stay on the bright side. Getting angry wasn’t likely to get them anywhere.

They emptied out all of their different pockets, seeing what possessions that they had. After they were done, it didn’t seem like they had much to help them escape; they didn’t have any weapons or sharp objects on them. All that they had was a cloth, a pack of gum, some rope, a few Band-Aids, an empty wallet, tape, a tissue and some candy wrappers.

“What good will any of this do?” James pouted, ironically sucking a lot of the optimism from the atmosphere.

Moments later, an evil smile popped out on Jessie’s face, and she said “I’ve got an idea. I know what we need to do,” with her smile not leaving her face for one second.

XXX

Officer Jenny strode down the hallways of empty cells, the only occupied one being the one that she had filled herself earlier in the week. She was carrying two bowls of soup to feed those very prisoners. She looked in the cell, and was shocked when she saw nobody in there. She gasped as she thought that they had managed to escape somehow. Little did she knew, James and Jessie were curled up tight in the front left corner of the room that was out of the field of the vision from the outside of the cell.

Officer Jenny unlocked the door and stepped inside, expecting to find a small passageway dug out through the wall. As soon as she stepped foot inside the cell, however, she was tackled onto the ground. She tried to let out a scream but her mouth was covered. Her brain then processed exactly what they had done, and the horror seeped into her mind.

She was unable to put up a worthy fight against her two opponents, and her mouth was soon covered with a white cloth that wrapped around her head with the help of a short string of rope. She soon found her hands cuffed together with a spare pair of handcuffs that she had been carrying on her belt. The two prisoners now looked down on her with matching smiles that did not give off any promising signs for her.

“Silly girl,” Jessie started, “Why did you decide to mess with the almighty Team Rocket? We weren’t even doing anything illegal! Well, it doesn’t matter why you did it, because I’m afraid that you’re going to have to pay for what you’ve done.” She sneered out in a threatening manner. Jenny tried to come up with a rebuke, but she couldn’t talk.

Jenny’s eyes shot open in a terrifying surprise as Jessie and James began to rip away her clothes. Her muffled screams became dramatically louder, they would have driven a person deaf if the sound waves weren’t blocked. Nonetheless, they were muffled, so her shrieks proved to be no threat towards getting the attention of a security guard or a civilian. Unfortunately for Jenny, the duo had shrewdly timed their attack while the guards were on their two hour break.

Once they finished stripping Jenny completely naked, Jessie gave a few unimpressed clicks of her tongue. “Well, it looks like you’re overdue for a haircut,” she commented, referring to her unshaven pussy. “We’ll take care of that for you,” She finished in false sweetness.

Jessie collected some of the Band-Aids that they had scrounged up out of her pockets earlier. She placed one directly over her a line of her pubic hairs, and ripped it off harshly once she had stuck it on. Muffles could once again be heard from Jenny as she struggled in pain. Jessie did the same thing twice more, until she had effectively removed the patch of hair surrounding Jenny’s vagina.

“What should we do with you now?” Jessie asked herself out loud.

“I think I’ve got an idea,” James answered for her.

They picked up the whimpering lady, and put her on top of the top bunk. James picked up the tape that lay with their assortment of “junk.” He put her left foot on the far side corner of the bed, and rolled multiple layers of tape around her ankle and the corner. He took her right foot and did the same thing at the other side of the bed. Once he was done, her head laid dangling down about three feet above the ground and her legs were spread as wide as they could go.

Jessie stayed on the top bunk where Jenny was hanging from, and James got back on his two feet. He dropped his pants to the ground, and pulled his shirt over his head. He freed himself of his boxers, and the untied the rope and took the cloth out of Jenny’s mouth

“You’ll never get away with th-” Jenny tried to give a threatening warning, but her mouth was once again prevented from talking; this time because of James’ cock being inside of it. She was utterly helpless; there was nothing she could do but take it. At the same time that James forced her to suck on his cock, Jessie got to work with Jenny’s exposed pussy.

She ferociously began to lick away at her clit, which drew more muffle noises to be emitted from Jenny. She couldn’t make much noise at all now, because James’ cock had hardened and lengthened since it had entered inside her mouth, and now reached back towards her throat. She knew that she would get smacked, and probably beaten even worse, if she attempted something foolhardy like biting down on his dick in protest, so she did no such thing.

“Oh yeah you suck that cock, you slutty little bitch, suck it good!” James commanded in ecstasy as he reached forward roughly groped her full chest. He didn’t bother being careful one bit, he squeezed, pressed, and pinched them as hard as he pleased. He’d never gotten to be rough the few times that Jessie and him had engaged in sex since she was pretty masculine herself, so he was enjoying his opportunity to do so now.

He pushed his long rod further in Jenny’s mouth while putting his hands on the back of her head to give complete control. He loved the pitiful gagging sounds that she made as she struggled to take in air with a big obstacle blocking the usual path. If that weren’t bad enough for her, Jessie was still lapping away at her other end.

As much as she despised herself for it, Jenny could feel herself getting wet down below. She was by no means enjoying this, but because of the stupid biology of her body, she was now releasing hormones. However, there was nothing she could do to stop it from happening. There wasn’t anything that she could do, period.

“Oh you like all this don’t you?” Jessie teased her as she started to realize the same thing that Jenny had. “Well, how do you like this?” She asked before inserting her index finger.

Jessie started fingering her roughly, much to the discontent of poor Jenny. She did not waste any time before adding her middle finger to join her index finger. Not long after that, she brought her ring finger in on the action as well. She pumped them in and out vigorously, causing for even more muffed up groans to escape Jenny’s throat.

Much to her dismay, Jenny reached an orgasm as the intense fingering continued. She thought that there was a slim ray of hope that it would all end now that she had reached her climax, but it didn’t pan out that way. Instead, she continued to lose the precious little amount of air that she had because of James’ dick, and she received even more teasing from Jessie.

“Oh you just love this don’t you, slut?” Jessie asked, “You want to cum for me again?” She kept teasing her.

Jenny did not even bother to attempt to shake off the outlandish claims. For one, it was not like it would help her cause, the questions were meant to be rhetorical. And two, it would not be wise for her to talk if she wanted to remain conscious. She knew that if James did not quit soon, that she would pass out. She didn’t think that it was very likely that he would choose to stop.

She was correct in that matter, James had no intention of stopping. He persistently shoved his whole member forward and brought her head forward as well, getting the deepest penetration possible, thanks to the angle that she was at. If Jenny was glad about one thing, it was that she didn’t throw up despite her uvula being knocked around some. It wasn’t much consolation to the fact that she was choking on dick.

Even though she knew it was useless, Jenny exerted some of her energy into trying to close her legs. It was a futile attempt; the tape had her locked into position well. The ceaseless finger blasting was getting close to making her lose control one more. It simply turned into a race of what would happen first; passing out, or cumming once more. Ultimately, she ended up climaxing once more, and only seconds afterwards, she blacked out due to her lack of oxygen.

She woke about 90 seconds later, still tied up, and the cloth was reinserted. She had been moved around though; she was now hanging right side up. Her arms were taped along the railing of the top bunk, her hands tied to the opposite corners. Her brain wasn’t able to process much, she was still groggy, but she had a pretty good idea of what was going to happen next. James was on his knees in the middle bed, and he lined up perfectly with her torso. Jessie remained on the top bunk, but now she, too, was nude.

Once he realized that she was up, James got right back to work. He pushed his full length in, pulled it out briefly, and shoved it right back in. Jenny let out a scream, she was finally able to get one out that wasn’t covered up, and then her mouth was soon covered by Jessie’s pussy. Jessie pushed on the back of Jenny’s head and demanded that she eat her out.

The terror and fear had sunk so deeply into Jenny at this point that she obeyed the command without any second thoughts of rebelling. She did not have any experience in this department, but tried to mimic the tactics that Jessie had used on her earlier. After her first few swirls of her tongue, Jenny immediately was overcome by the acrid taste. It was horrible!

“Oh you love eating out my pussy don’t you, bitch?” Jessie kept on with her unabating and humiliating taunts. “You’ve done this before haven’t you? I’m sure you have. It’s your favorite food isn’t it?”

Jessie’s accusations were so incredibly accurate, but Jenny knew she had to put up with it. She kept telling herself to not show any weaknesses, just power through; it has to end eventually. The thrashing that she was taking was hardly bearable, however. James gave no regard to the fact that her seldom used vagina had a tough time fitting him inside her, or that he was causing some intense pain. He had mostly started this ordeal just to comply with Jessie, but some strange feelings had overcome him and caused him to enjoy his dominate position.

The angle created from Jenny hanging down allowed for James to reach into depths that no man had reached for Jenny before. He had no hesitation in getting the most out of this advantage, he roughly slammed his entire member inside her, repeatedly. The pain was too much for Jenny to ignore, she had to tear her mouth away from her disgusting chore, and grit her teeth to prevent shrieks.

“How dare you stop?! I didn’t give you permission to do that! You’re going to have to pay for that!” Jessie exclaimed.

Jessie climbed over the railing and hopped onto the second bed with James. She said something quiet enough that Jenny could not hear, and James pulled out of her. Jenny was extremely confused as to why he did so, but felt some short relief. The relief was ephemeral for sure, James entered back inside of her moments later, but this time, it was in her other hole.

“AHHH!” Jessie let out a deafening scream as her anal virginity was roughly stripped from her. She thought that her vagina had a tough time accommodating James’ size, but this was on an entirely different level. She felt her inner walls swell and stretch out further than they should, or she even thought they could. She could not even attempt to hold back from screeching painfully loud.

Because of this, Jessie hurriedly grabbed the cloth back up and put it back inside her mouth. It greatly reduced the loudness of Jenny’s yells, but the muffled noises coming out were significantly louder than the ones she had made earlier. Just when Jenny thought that it was as bad as it got, she felt Jessie reenter her fingers back inside of her vagina.

She was expecting more fingering, but got a terrible surprise when she felt Jessie working around to fit her whole hand in. After some wiggling around, Jessie was able to get her balled up fist inside of her, and she began to fist her. Now that both of her holes were being filled with more volume than she thought was possible, Jenny felt a few tears start to stream down from her face.

She no longer worried about not showing weakness or pain; it hurt too badly. She openly sobbed, and her muffled screams of agony were loud enough that if anyone else was in the building, they would have easily been audible. Her pain was not enough to touch the hearts of her assailants; there was no letdown in their activity.

As her pussy continued to be violated by the rough thrusting of Jessie’s hand, Jenny felt herself orgasm once more. It was the most powerful orgasm that she had ever had, but it certainly did not feel good. Jessie retracted shortly after she felt her hand get sprayed with the juices that flew out of Jenny. She got up and got back on the top bunk once more. She loosened up the cloth just a little so that she could fit her hand inside of her mouth.

“Suck your own juices, bitch,” Jessie snarled out venomously.

Jessie slipped her index finger inside of her mouth, making Jenny give it a sufficient cleaning. Once she felt that she had done enough, Jessie put her middle finger in for a cleaning as well. She did the same thing until her whole hand had been licked off. Meanwhile, Jenny felt so dirty and disgusting. Sucking on her own cum? Just the thought made her want to throw up.

Before Jessie could come up with any new, cruel way to humiliate her, Jenny felt James finally shoot off his load inside of her. He had managed to abstain for quite some time, but in finally doing so, he was able to get one final climax from Jenny as well. She closed her eyes and whimpered at the extreme suffering she had just been put through. She knew by the amount of cum that had been released into her anus hat James had to be spent, and that they were done with her. Or at least close to done.

To confirm her suspicions, she felt the tape being undone from her arms, and she fell the four feet that her feet were hanging from. She was hanging right side up, but she did not have the focus or energy to land on her feet. She collapsed onto the ground in a pitiful heap. Jessie and James began to redress themselves while Jenny felt James’ cum slowly start to leak out of her butthole.

Jessie piled up all of Jenny’s clothes, and grabbed the key to the jail cell as well. She walked over to Jenny one more time, and lifted up her face. The face that she saw was covered in the tears that she had produced over the last 10 minutes. Her caramel brown eyes could hardly be seen through the squint and all the tears.

“You don’t mess with Team Rocket, ok bitch?” Jessie cleared her point one final time before she escaped.

Jenny gave a slight, trembling nod. Jessie gave a short, satisfied snort before opening Jenny’s lips with her own, and spitting a large ball of saliva down her throat. She then put the cloth back over her mouth, and tied her down naked on the bottom bunk. With that, Jessie and James left the cell for good, feeling that they had gotten their revenge.

They closed and locked the door behind them, taking the key with them. They fled the city right after they got out; they weren’t sure how many minutes, hours, maybe days, it would take before someone would find out about Jenny. All that they knew was that anyone who dared try to incarcerate them was in for some big trouble.


	10. Judicious

**Summary for the Chapter:**

> Cynthia is faced with a tough decision when one of her students is failing, but she makes the right call.

It was Friday, June 1st, the last day of school. Ash had completed his final exam of the year, geometry, that morning. He stuck around until the end of the day because his class was throwing an end of the year party, and he thought it might be fun. It turned out to be a pretty good time, but as the clock inched forward, everybody there was anxiously waiting for the final bell to ring.

“Can I get a kind student to stay after and help me clean all this mess up?” Ms. Gray asked, before adding “It will only take a few minutes!”

Ash was quick to volunteer, he didn’t have anywhere to be so he did not mind. The bell rang shortly after, and the school’s halls were soon filled with delightful whoops and excited cheers from the students who were officially on summer break. Ash smiled at the happiness that radiated from the departing student body, but then remembered that he had some work to do.

He took the trash can around the room, and filed it full of candy wrappers and other trash that the class had left sitting on the floor and desks. As his teacher had promised, it did not take him long at all to finish his part of the cleaning. She had been sweeping the floors, and upon finishing her job, she called Ash over to her desk before he could leave.

“Can I speak with you for a minute, please?” She kindly asked, though there was only one correct answer.

“Uh, sure. Is something wrong?” Ash was scared of what might come up.

“It’s about your exam. Well, your grade in particular. I’m afraid that you came up just one point shy of passing. I know how hard you have worked this year, and I just hate this. I mean, you came to tutoring, you were nice enough to stay after here today, you always do your homework; I know you have the right work ethic. Math just isn’t your forte. But I would like to help you out.” She finished with a friendly smile on her face.

Ash was stunned. He knew that he was not a good math student, but how could he fail! He felt sick. Why didn’t he just study a little bit longer? Why didn’t he go over his exam one more time? His mom was going to kill him for this! Before he ventured too far down the road of consequences, he remembered that Ms. Gray said she would like to help. Maybe there was hope after all.

“What exactly do you mean by that?” He asked, crossing his fingers.

“Well I was thinking I could give you some extra credit; enough so that you can pass this class.”

Intense relief washed over Ash when he heard these words. He could pass after all. He had managed to get his teacher to like him enough for her to help him out. He hated her class, but he really liked Ms. Gray. She was extremely young for a teacher; she had to be in her twenties, and she was very nice and helpful. He had to admit; she was really attractive. He tried not to think about his own teacher like that, but he couldn’t.

“What would I need to do for this extra credit?” A much calmer Ash asked.

“I haven’t decided that just yet. I’m sure we could work something out.” She finished with her soothing smile still present.

After chewing on her lip briefly, Ms. Gray got up from her desk and walked around to the same side of her desk that Ash was on. She was wearing a sleeveless, celeste top, a pair of long, black dress pants, and some short pump heels. Her long, luscious, blonde locks flowed smoothly down past her waist. She eyed Ash briefly, seemingly judging something about him, and nodded confirmation to herself after her contemplation.

She got out a piece of paper and reached for a pencil to start to write with it. She started writing a few words, and she spoke as she wrote them down.

“How about you help me out with- oops!” The pencil she was writing with managed to slip out of her grasp and rolled around on the ground.

She bent over to pick it up, purposely bending her back and knees in a way that her shirt would scoot up, and wiggled in a way to shimmy her pants down a little bit. She pretended to fumble around with the pencil, waving her slightly exposed ass in Ash’s face. The only thing that gave her a little bit of coverage was some forest green underwear.

Once she thought she had stayed in her position for a sufficient time, she turned around and looked at Ash. His face was turning red, and he avoided her look. She smiled, knowing very well that he must have had a good luck at her. He, at this point, was obviously oblivious to her intentions. She glanced down at his lower body, and gained all the confirmation she needed.

“Yeah I think we can work something out right here and now,” She stated in a softer voice as she rubbed her hand over his bulging erection.

“Wh-what do you mean?” Ash had lost his tranquility at this point.

“You’re a smart man. I think you know what I mean.” She responded.

Ash was almost too stunned to remove as what his math teacher was implying to him. He almost didn’t realize what she was doing until he felt the pain that his suddenly too tight jeans had been causing ceased. He had been wearing a two-button orange polo, but he realized that it was no longer attached to his body. His raging erection was now only limited by his red boxers, but those, too, were soon lost.

“Ms. Gray! What are you doing?” Ash regained his ability to talk.

“Please, Ash, call me Cynthia.” She responded as she licked her lips.

She gave no time for Ash to object, not that she expected him to; she was just impatient. She took his member in and started sucking on it. Ash had managed to convince himself that this was not a dream, and after overcoming the pure shock of the past minute, he succumbed to the pleasure that he was feeling.

“Oh Cynthia…” He softly cried out.

He had received a couple of blowjobs from his classmates before, but they paled in comparison to what he was getting now. Despite her young age for a teacher, she still had quite a few years on Ash, and would be considered a veteran in this field. Her wet mouth moved skillfully up and down his shaft, causing immense joy for Ash.

“Oh yes” He moaned as he continued to enjoy Cynthia’s dirty work.

She looked up at him with her light brown eyes opened wide, aiming for an innocent façade, while she slowly took one, long lick over his full length. Just to change things up a bit, she moved down and pleasured his balls with her mouth. She sucked on both of them with her moist mouth, making Ash an even happier man.

“Oh my god, yes!” Ash now recognized that staying after today was his best decision of the school year.

Cynthia moved back to the main attraction, expertly finding a way to fit Ash inside of her with no problem. She seemed to have a fair amount of experience; she was adept with the use of her tongue. Every part of him was getting the gratification of having Cynthia bob her head up and down, repetitively.

“Cynthia!” Ash called her name as he knew he was getting close.

Cynthia made no flinch or acknowledgement that she heard, she just kept working on her task. Seconds later, Ash finished with a cry, and he sent his sperm spraying into her mouth. She swallowed it easily and eagerly; she even sucked on his tip some more to make sure that there weren’t any leftovers. After she had gotten every last drop, Cynthia rose up off of her knees.

“What’s it like to get sucked off by a real women?” She asked in a husky voice, taking a jab at the girls that Ash had alluded to earlier.

“Fucking amazing” He responded coolly.

Cynthia refused to wait any longer, and she yanked her pants off quickly. She took a little more time to be careful with her nice shirt; there was no need to ruin her clothes. Ash was only able to get a look at her matching underwear that was the color of leaves in the spring before her bra was discarded as well. Her C cup breasts popped out; her nipples were hard and perky.

“I haven’t been with a man since I became a teacher. I need this.” She claimed in a desperate voice that certified that she did need it.

Ash was still hard despite already releasing once, and he was ready to go. Cynthia bent over her desk, and slid her panties down to her ankles, where they hung just above her heels. She flipped her long hair off to the right side, and waited as patiently as she could for Ash to get started. Even though it was not a long wait, it seemed eternal to Cynthia. She was as wet as a pool down there and she was getting anxious.

Both of them released simultaneous gasps when Ash finally pushed inside of her wet entrance. Since Cynthia had gone so long without having sex, she was very tight. Her insides clamped down on the intruder, creating more bliss for Ash. Every nerve on his rod was sending back waves of pleasure due her walls squeezing him tightly.

“Oh I’ve never taken anyone this big before,” Cynthia cooed.

It wasn’t just a lie to boost Ash’s self-esteem; she really hadn’t ever taken anybody that big before. He wasn’t some freak of nature that couldn’t even fit, but he was big enough to stretch her out further than she ever had been. The long break that she had endured between her sexual interactions was all a part of a distant, unimportant past. None of that mattered; the wait was worth it.

“Deeper, Ash! Harder!” She demanded, wanting for her wonderful feelings to multiply.

Slightly surprised that she wanted to bump it up a level so quickly, Ash took a little bit to react to her wishes. However, he did not ignore them, and soon gave her what she wanted. He no longer gave timid, half pushes, and he started to get more intense. He now penetrated as deep as he could, making Cynthia give off powerful gasps.

“OH! Oh yes!” Even though she saw how long he was, she was still surprised at how far he managed to reach.

He penetrated to places that she had never had touched. She bit down on her lips and tongue to try and prevent herself from getting too loud. She was sure that most of administration was still on school grounds and if any of them ventured too close to where she was right not, her job would be in major jeopardy. Forget jeopardy. She would be fired on the spot.

“Mhm! Oh! Faster Ash, faster!” She pleaded out in a softer voice now that she had acknowledged what could happen if they were heard.

Ash smiled at this request, now he felt that he had the freedom to go all out if he pleased. He started to pump in at a much faster rate, multiplying his speed. He was still going all the way in, and each time he pushed to as deep as he could reach, a smacking noise was created. He felt in control of his teacher, a role swap that was interestingly enjoyable for Ash.

Cynthia, too, found herself enthralled by Ash’s actions. Between the fact that she had gone so long without a man, and the fact that Ash was quite a man for his age, it was the best sex she had ever had. She knew that he was still an amateur at this, but he was catching on pretty quickly. With even more practice, he could be a golden catch for whoever ended up with him.

“Oh yeah! Just like that! Make me cum!” As great as this felt, she wanted to have her orgasm.

Ash understood that the end was near, and he gave it everything that he had. He pumped in and out of her a rigorous pace, roughly entering and exiting her over and over. He felt a few beads of sweat start to drop from his body, and just at that moment he realized how much energy he had been expending. He used his last reserve to make the final seconds as fantastic as possible.

“OHHH! OH! AH!” Cynthia screamed louder than she would have liked when she climaxed.

Ash pulled out hurriedly as he was coming to a close as well, but he didn’t want to finish inside of her. Instead, he spun her around and dropped her down onto her knees, where he sprayed her with his second round of semen. Ash wished that he had a camera at this moment, because the sight of his beautiful geometry teacher with a face splashed with his cum was a sight he never wanted to forget.

They were both taking deep breaths to try and get some of their energy back. Cynthia closed her eyes and tried to relive what she had just gone through. It was the most physically pleasing moment that she could ever remember. She now knew that she had made the right decision in letting Ash gain his extra credit.

“I don’t know Ash,” She started, sounding unsure, “after what you just did, I kind of want to hold you back for another year.”

“Oh don’t worry,” He responded, “I’ll come back for some more tutoring.”


	11. Kinship

**Summary for the Chapter:**

> Ash has never been very fond of his girlfriend's sisters, but when he gets spending time with them, he finds out they aren't that bad.

Ash sighed as the gym doors closed; Misty had left despite his protests. She said that she had private errands to run, and she wasn’t going to be back for multiple hours. Ash offered to go with her, more like pleaded, but she insisted that she had to go alone. Now he had to spend the rest of his day at the Cerulean Gym with her sisters. He really wished that he had not left Pikachu at the Professor Oak’s lab now; he could use his little buddy as a companion. Ash groaned again at the depressing thought of being alone with Misty’s sisters.

Sure, they were all extremely attractive, but they weren’t exactly the brightest of the bunch. And neither was Ash, so if he thought that they weren’t very smart, then they must not have been. Not only that, but they were painfully annoying, with all of their “likes” and high-pitched giggle fits. He hoped that they would stay to themselves today, and he wouldn’t have to deal with them.

Before he could come up with a solid plan to ensure that he spent the next few hours in solitude, he heard a series of giggles coming from the hallway. His breath stopped, and he braced himself for the pain that was almost guaranteed to accompany the ensuing conversation. Sure enough, Lily, Daisy, and Violet emerged from the hallway, and they immediately noticed Ash slumping on the couch in the lobby.

“Hey there Ash!” Lily called out to him, “Are you, like, ok?” She asked because he obviously did not look very happy.

“Oh I’m fine,” Ash assured her, “Misty just ran out of town, and I was just doing some thinking.” He said, and added silently, something you guys should give a try.

“I don’t want to get in you girls’ way, so I think I will head back to Pallet Town. Can you let Misty know that I’ve left when she gets back?” He asked them while putting his jacket on in preparation for facing the harsh winds outside.

“Oh that is nonsense!” Daisy responded, “You won’t, like, get in our way. We would love to have you here!”

Crushed that his escape attempt was blocked, Ash feigned a smile at the request to stay.

“In fact,” Daisy continued, “We were about to, like, rehearse for our next water show, and you could come, like, watch if you want.” She finished as her sisters nodded in agreement.

“Sounds great!” Ash responded, only half-faking this enthusiasm.

Watching one of their water shows wouldn’t be too bad he figured. It did not require any conversation, and the few shows that he had attended had actually been pretty entertaining. Not only were they gorgeous, but the girls were really talented as well. There was a reason that they were called the Sensational Sisters.

So Ash followed behind the girls en route to the huge pool that served as both a battlefield and a stage. He escorted himself to the viewing bleachers while the girls prepped for their rehearsal. He started to drift back into his thoughts, and was unaware that the show had begun. He really wanted to know why Misty had been so adamant to go by herself, and why he had to get stuck back here.

Luckily for him, Ash stared straightforward as his daydreaming of the different possibilities of what Misty had to do played in his mind, so the girls could not tell that he was not paying any attention. To them, it seemed as if he was staring captivatedly as they performed their spectacle. Before Ash even managed to get out of his daydreams, the show had ended, and Misty’s sisters came up to approach him once again.

“So, like, what did you think?” Violet asked, running a hand through her wet, blue hair.

Ash shook his head to wake himself back into reality, and his brain quickly comprehended what had happened to him.

“I thought it was fantastic!” Ash said, flashing a smile. He figured it wasn’t really a lie since he didn’t know if it was good or bad.

“Thanks!” They said in unison, all of them beaming.

It was at this moment that Ash really got a good look at the girls. Daisy, the closest one to Ash, was wearing a not-so-modest dark red two-piece swimsuit. The water she had absorbed was causing her bathing suit to tightly adhere to her skin. Ash could see just about all of her. As he eyed over Lily, he noticed that the same thing had happened to her cobalt blue bikini. He then directed his attention over to Violet, and his eyes nearly popped out.

She was wearing a carnation pink bikini, and due to the soakage that she had received, Ash could see through the fabric. If he was an intelligent man, he would have immediately averted his glance and never looked back. Unfortunately, Ash was rather fascinated by the sight, and he kept his eyes locked in on it for too long. It did not take Violet a long time to realize that Ash had his eyes on her, and she quickly looked down and noticed exactly what he was seeing.

Her eyes opened a little wider in surprise, and she cast a questioning look at Ash with those eyes. His skin turned into a dark, crimson red as he blushed profusely from being caught. He avoided her look, and scolded himself mentally. He felt sure that a verbal thrashing was about to come his way, and it was quite possible that a physical thrashing might follow that. Not only that, but if she spread word to Misty, than he could kiss his relationship good-bye.

Unbeknownst to Ash, Misty’s sisters were actually really jealous of Misty in one aspect; him. They grew up as the prettier, more popular sisters, and they had always given Misty a hard time about it. They could hook up with just about anybody at a club or party, yet Misty was the one who ended up with the most desirable man. Ash was tanned, fairly muscular, made a very solid income, and according to Misty, he was something else in bed.

So as Ash was expecting for the worst, the girls, Violet in particular, were thinking of a way to exploit Ash’s mistake. Since Ash was covering his face with his hands in regret, it gave the girls an opportunity to silently communicate without him noticing. They all locked eyes and a grin took over the faces of all of them at the same time. They all knew what they wanted.

While Ash was still hiding his face, Violet slipped the bottom piece of bathing suit down her legs and kicked it out of the way. She undid her top piece next, throwing it and landing it on top of the other half of her bikini. For most siblings this would be an extremely awkward, embarrassing, unforgettable, and scarring moment. However, the Sensational Sisters had shared a man before, and they were completely comfortable around each other.

“Ash.” Violet said his sternly, giving Ash the impression that she was pissed off. He slowly started to peek his eyes out, knowing that he could not hide forever.

“Is this a better view?” She asked with a sultry smile.

Ash’s jaw dropped and stayed that way. What was going on here? Was he seeing things? No, this all felt too real. What the hell was Violet doing? Why would she pose naked for her sister’s boyfriend? One that was just inappropriately staring at her? Why were Daisy and Lily seemingly ok with his? Shouldn’t they be appalled by this? Why were they letting this happen? Why was this happening in the first place?

Seeing that Ash was not going to form any words, Violet got even bolder. She sauntered over to where Ash was sitting, frozen in disbelief, and she stood up over him. Trying to make up for his last mistake, Ash covered his eyes and attempted to move his head out of the way. The girls giggled at his obvious discomfort and misunderstanding of what was going out.

“I don’t think you understand, Ashy.” Violet started, “You’re going to eat me out.”

Ash was still having trouble accepting what seemed to be going on, and he was both worried and confused. Violet noticed that he was having a tough time choosing his actions, so she made up his mind for him. She shoved his face up into her crotch, and that was able to get the message across clearly.

Ash, with a fair amount of reluctance, began to use his tongue on Violet. He’d learned a few things from the times that he had done this to Misty, and he was curious to see if Violet had the same weak points that Misty did. Sure enough, as he pressed up against points that would drive Misty crazy, he could feel Violet tense up and could hear moan in happiness.

“You know what you’re doing don’t you? Oh that’s nice!” Violet let out while her sisters looked on in jealousy.

Lily and Daisy were getting turned on by the action that their sister was getting, and they wanted to get in on the fun as well. Seeing that the other two people in the room were taken, they knew that would have to use each other. It was not something that they did on a regular basis, but they had been together before. The Sensational Sisters did not consider themselves bisexual; they were not attracted to other women, but they had no problem when it was just them.

So they fiercely brought their lips together, and allowed their hands to roam up and down the curves that the girls had developed. In the process of admiring each other’s bodies, they managed to work the clothes off of one another. As they continued to hear Violet moan in pleasure, they knew that they wanted the same thing. They broke their lips apart, laid down, and got into a sixty-nine position.

Meanwhile, Ash had excelled in his work enough to get Violet off. She sprayed her juices right into his mouth and got a little on his face as well. Ash thought that it tasted tart, and he did not want to swallow it, but he knew that he was not in a good situation currently and was afraid to make any of the girls mad. He cleaned it up without any verbal complaints.

Now that his eyes were free for the first time in the last few minutes, he was able to see what Daisy and Lily had gotten up to. He never dreamed that he would see all of the Sensational Sisters naked, and not only that, but also getting in on some lesbian action. He felt his penis turn rock hard, and he had to remind himself that this was not just a wet dream.

“You aren’t off the hook yet,” Violet let him know as she saw his little friend begging to see daylight.

She started undressing the only person in the room who remained in any clothing. Ash had now gotten over the initial uncomfortableness, and was fully on board with the current plan of action. He assisted Violet in getting himself naked, and soon, he was just so. Violet started to straddle him, but she was interrupted by Lily.

“Hey, no fair!” She whined, “You already had your turn with him!”

She was evidently tired of fooling around with Daisy, so she marched across the gym and demanded that she got to have her turn. Violet reluctantly let Lily have her way, and she backed away. Lily then took the cowgirl position that Violet had wanted, and she lowered herself down on top of Ash’s cock.

“Holy shit! Oh it’s so big!” She moaned out as she grinded up against him.

Ash’s beast provided a test for the well-tested walls of Lily. Even though she had picked up plenty of men; she had not had a man with the size of Ash. It wasn’t the length of him that was problematic, no she had seen multiple dicks with the same length, but it was the thickness that made him such a tight fit.

Just using an eye test, his base looked about as thick as her wrist. Instead of being intimidated by such a challenge, she took it on with open arms. It caused for some serious friction to be created as she continued to ride on him. She was still taking it slowly, but it was more of a slow bounce than grinding at this point.

“Oh! Oh my god! So good!” She softly moaned with closed eyes.

The speed of her bounces escalated as she acclimated to having such a thickness within her. She tried to put most of the work on herself since she knew that Ash was going to have to last through at least one more round after she was done with him. He simply sat back against the bleacher and let her go to work on him.

Before long, she was releasing loud shrieks while she rapidly rode on top of his member. She hadn’t had a man make her feel this way in a long time, and she was relishing every moment with him. He filled her to the brim like nobody had been able to do since she lost her virginity. Eventually, it all got to be too much, and she gave out after a few more minutes.

“OHH YESS!!” Lily let out one final scream while she powerfully orgasmed all over Ash’s crotch.

She would have liked to stay in her position for a few more moments, or even go at it again with him, but she knew that her sisters both wanted their turns with the man of the evening. She got off from him and collapsed happily onto the floor. With Lily out of the equation for the next sequence, Daisy stepped up to the plate.

She approached Ash, and lightly pushed against his chest to make him lean back. She set her feet onto the second row of bleachers where Ash’s head was, and she flung her head and whole body back, holding herself up with her hands on the floor. Her full beautiful body was on display for Ash, and her torso was hovering just above his.

“Go to town on me, honey,” She said lustfully.

Ash thought about pinching himself at this point, but withheld from doing so. He instead chose to waste no more time in attacking to opportunity that was given to him. He pushed himself inside of her, and stayed in for a few moments, giving her time to prepare. He then started to enter and retract at a modest pace while admiring her body.

Her breasts were a modest size, he figured something like a B cup, and her stomach showed no signs of fat whatsoever. In fact, there was no sign of fat on her toned arms or legs or anywhere else on her. Her face had no imperfections, and she had long, beautiful, golden hair. She had everything that you could ask for.

He chose not to wait spend much time at the more loving pace, and soon got more rough with her. He picked up the pace which made Daisy scream like crazy. She had asked for it, and Ash was delivering the goods. Daisy had not been with a guy in months because she was trying to get together with Tracy, but she had to make an exception for today. She and her sisters had fantasized about sleeping with Ash since Misty and he had become a couple.

“OH GOD! YES!!” Daisy yelped due to her treatment

Getting bored from her lack of action, Violet thought she would put her rack to good use. She moved over to where Ash and Daisy were and pressed her breasts, she had the biggest out of the three of them, into Ash’s face. Despite not being able to see his target, Ash kept pumping away into Daisy.

Lily had gotten out of her high state, and wanted back in on some action as well. Partially to try and mute her sister, and partially because she wanted the pleasure, she sat over Daisy’s face and let her start to lick at her pussy. The noise echoing from the room went down dramatically now that Daisy wasn’t voicing her happiness as loud anymore.

Ash had already felt Daisy orgasm once or twice, but she did not want to relinquish her position with him, and that did not bother him one bit. He was giving it to her full strength now, and she was taking it like a pro. He found all of the Sensational Sisters to be gorgeous, and that included Misty, but he had to admit, Daisy was the best looking of all of them. If had to choose just one of them, he would choose her, but luckily for him, he did not have to.

Not only was he nailing Daisy, but he had a fantastic pair of breasts right in front of him. Since his hands were free, he was able to rub and pinch well sucking on the other one. Violet was giving off very soft, yet very frequent, gasps that she almost seemed to be attempting to keep in. It was at this heavenly moment that Ash officially decided that there must be a God, and he must be one nice guy.

On the other end, Daisy had adroitly used her tongue to make Lily reach another climax. This time, she hit the floor and had no intention of getting back up anytime soon. Daisy did not even bother to grit her teeth now that her mouth was free; she was having a magical moment and she was going to let everyone else know about it.

“OH! OH! OH! FUCK ME! FUCK ME JUST LIKE THAT!! OH YEAH!! OH!!” She shrieked happily.

Ash, however, was gritting his teeth for a completely different reason. He wanted to postpone his release for as long as he could, for he knew that he was going to spent was he let his load go. He had powered through for this long, and he just kept pushing himself to make it even further. Each second that he kept going was another fantastic second, so why not go as long as possible?

Ash was actually proudly surprised at how well he was doing. The girls had cummed a handful of times combined, yet he still had not finished himself. Also, he could hear from the thumps that rang out with each entrance that he was giving it to Daisy extremely well. He could tell that from the noises she was emitting as well.

“OH MY FUCKING GOD!! AHH! OH! AHHH!” Daisy climaxed one final time.

This time, she decided that she had gotten more than her fair share, and that she was done. She got off of Ash, and laid down next to Lily, leaving Violet as the only one standing. Violet figured that Ash would not be able to handle another round of regular sex, and upon seeing his dick coated with her sisters’ juices, she thought she would settle for oral sex.

“Time to finish what I started,” She said with a smile as she got onto the same level as Ash.

She dropped down to her knees, and let Ash be the recipient of a tongue’s work this time. She took in his cock, which had a strange taste due to the juices on it, but she liked the taste of it. She used her hands to play with his balls while she bobbed up and down on his rod. With her fair amount of experience, she was able to fit all of him in.

She moved her tongue around like a snake, coiling around his shaft, touching all the right places. Ash groaned loudly in approval to her wonderful work. She thought nothing of it; she was used to impressing men like this. Before she could get too serious with her work, Ash pulled her head off of him. For a split-second she was confused as to why, but her question was swiftly answered.

A seemingly endless string of Ash’s cum splashed onto the face of Violet as his miraculous run finally reached a close. He had held on for so long that he had plenty of sperm to unload, and he shot it all onto her. She knew that her face must have been pretty well covered in the sticky liquid, but she did not mind.

Even though Ash thought she looked really cute right now, he felt waves of guilt run through him. The sisters of his girlfriend had just seduced him, at first just to make up for his staring, but he let them carry out the act. He knew that he had cheated on Misty, and he just hoped that either she would not find out, or it would not end his relationship with her.

Sensing what Ash was feeling, Violet spoke up. “Don’t feel guilty Ash. After all, it isn’t cheating since we’re family.”


	12. Lust

**Summary for the Chapter:**

> Ash encounters a feeling that he is unfamiliar with when he meets Giselle, and some role-play ensues from it.

Ash’s face held a huge smirk as he scanned over the battlefield. He had made easy work out of Giselle, supposedly the top student in the academy, and he was making no attempt to conceal his satisfaction. Giselle returned her cubone with a little bit of a pouty look, but she voiced no unhappiness. In fact, she looked unsurprised by the outcome, like she had expected to lose, but that did not mean that she was not disappointed.

Giselle had acted like a jerk to Ash’s new friend, Joe, a novice Pokémon trainer, and she also talked condescendingly to both Ash and Misty. She spewed out meaningless trivia, and cold insults when Ash and his companions had stopped in at Pokémon Tech to assist Joe. When they arrived and had their first confrontation with Giselle, Ash’s eyes almost popped out.

He’d never seen a more beautiful girl in his life. It probably helped her cause that the only comparison that Ash had for her at the time was Misty, a girl who honestly seemed more like a boy to him at the time. For once, Ash joined Brock in ogling a girl. After getting to know her, Ash realized that he did not care at all for her personality, but that changed nothing for his physical attraction to her.

She had waist-length dark brown hair that had a few waves in it. She had big, wide, light brown eyes that contrasted with her hair. She wore a tight mini-skirt that was likely mandated by the school she attended. She also wore long, white stockings that came up past her knees. The only way that she could have looked any more like a stereotypical schoolgirl was if she had hair in pigtails.

Lost in admiring her, Ash barely noticed that Giselle had retreated from the battlefield and gone back inside. He knew it was immature, but he wanted to track her down and rub it in her face anyway. She had put a verbal assault on him and his friends, so he felt that it was only right to dish it right back at her. After excusing himself from his friends, and leaving Pikachu in their care, he headed in her direction.

He ended up finding her in a room that greatly resembled a locker room, though it was highly unusual that a school would have a locker room for Pokémon battling. However, this was a rich school dedicated to Pokémon training, so it wasn’t all that strange really. Giselle had her back to him when he entered; she was putting her bag away into her personal locker.

“I expected more out of Pokémon Tech’s ‘top trainer.’” Ash said, putting air quotes around his last two words.

Giselle turned around to face him, but she was unfazed. She looked at him emotionlessly, her eyes conveying that she was either really sad, unsurprised, or just plain didn’t care. She gave a huff that was practically silent, and she gave no response. She simply stared Ash down and waited for him to continue with the taunting.

“How did you even get into such a prestigious academy when you clearly can’t battle well?” he asked, both to enrage her and because it was a legitimate question.

When no response came again, Ash continued, “I bet a girl like you got in just because of looks.”

Giselle had turned back to her locker, but spun around after his accusation. He had managed to rile up some sort of emotion from her this time around. To his surprise, Giselle wasn’t shooting fiery daggers at him. Instead she looked at him shockingly, her mouth opened. She wasn’t mad; she was just stunned.

“You’re right.” She said, quietly.

“What?”

You’re right,” She repeated, “I just did a few favors for the guy in charge of admission.”

“You slept with him?!”

“Yep.” She said, shrugging her shoulders nonchalantly

“You know I could report you for that! That’d get you kicked out, sent to court even!”

“But you won’t.” She said calmly and truthfully.

“What makes you think that?”

“Because you want me. Just like the man who let me in here wanted me.” She alleged.

“Well… maybe.” Ash conceded.

“That’s right Ashy.” She purred, getting really close to Ash.

“We’re going to do this my way though.” He stated firmly, and then he proceeded to inform her of his wishes.

XXX

15 minutes later Ash marched back into the locker room that he had been in with Giselle previously. When Ash caught sight of Giselle, she was stuffing something away in her green backpack. Now her hair was done into two long pigtails to complete the schoolgirl image that Ash had requested for the ensuing roleplay. He walked up behind her and scared the living daylights out of her. She hadn’t realized that anybody else was in the room.

“Let me see that.” Ash commanded.

He took the bag out of her hands and began to rummage through the content. Tossing away a pair of notebooks and a few magazines, he came across a crumpled up set of stapled papers. He unfolded them to the best of his ability and scanned over it to see what she had been trying to hide. He quickly realized that it was a copy of the test she was going to take tomorrow, with all of the answers filled in.

“It’s not mine I swear! Someone just gave it to me!” She said frantically.

“Come with me.” He said sternly, turning away and walking towards the coach’s office.

He opened up the door to the small room, and shut it loudly after Giselle had gotten in. The room had a long table with paperwork scattered around it, a whiteboard, and two stools on both sides of the table. Ash sat on the side that would belong to the teacher/coach, and Giselle took her seat on the opposite side, not liking how far down the stool was.

“How did you get this?”

“Someone gave it to me!”

“Stop lying!”

“It’s the truth!”

“You realize that I could give you a lengthy suspension for having this? And then lying about it to cover up? Heck, you could be expelled.”

“You won’t do that, will you? She asked, terrified.

“Well, what do you think your consequence should be?”

“I didn’t do anything!”

“That’s enough, I’m sick of this lie!”

“But Mr. Ketchum!”

Giselle was getting flustered since she was getting nowhere with her teacher. She was starting to get extremely worried that she could get serious repercussions, such as expulsion, for this. She noticed that her teacher was fumbling with something across the table. Was he reaching in the drawer for something? No. His pocket?

“I don’t want to hear another word from you!” He said, standing up and revealing that he had undone his pants.

“WH-WHAT?!” Oh no! Not this!” She eyed out the windows, hoping somebody was around.

“It’s this or you get kicked out from here and start your career over from scratch.” He said, putting Giselle in a tough situation.

“But w-” Giselle couldn’t finish her sentence because Ash had made her decision for her.

“I said I don’t want to hear another word.” Ash said as he lifted his hand off her head.

Giselle could not believe what was happening. Her teacher accused her of a deed that he couldn’t prove, yet he threatened to kick her out if she didn’t pleasure him. She didn’t think she would have been able to make a choice on her own, so in that aspect she was kind of glad that Mr. Ketchum had chosen for her. That being said, it still wasn’t a happy time in her mind.

She was beyond uncomfortable having her teacher’s penis in her mouth. She began to slowly bob her head up and down; she hoped that if she started to go along with it then maybe it would not be as bad. She even used her tongue to lightly lap along the bottom of him. She was still very tense, and she still was praying that somehow this would end.

With each passing second, it became apparent that they were the only people on this part of campus. Everyone else was likely back in their rooms since it was starting to get pretty late. Ash tossed his shirt off, and he grabbed one of her hands and guided it up to his ball sack. He left it there, knowing that she understood what he wanted. She began to caress his balls while she caressed his rod with her youthful tongue.

“Oh yeah!” Ash groaned as his student went to work on him.

Seeing that she wasn’t going to do any more than she was asked for, Ash took action. He put his hand behind her head again and forced her to take all of him in. He held her there while she made gargled choking noises. He brought her back up once he felt he had gotten enough treatment down there, and then forced her right back down.

Ash started to rapidly force her head up and down. He would push her as far down as he could, causing her to gag when he started to crawl down to her throat, and he would bring her back to a comfortable position briefly, before forcing her back down. After repeating this for this a little over a minute, he let her come all the way up and breathe.

She gasped, taking in deep breaths. Once her breathing started to calm down he forced her back into the same process. She was getting turned on by the rough treatment, yet she could hardly take it. His cock was mammoth, and it rammed itself down her tiny throat each time that he forced her to take all of him in. He was pressing her up and down as fast as he could, so she never had time to choke, nor did she have time to recover from the quick cutoff to oxygen.

Finally, the feeling of Giselle’s throat muscles rubbing against his member started to cause him to lose control. He brought her head all the way down one final time, not letting her back up this time. She sat gagged on his meat, choking violently. Ash stayed firm though, and then released his seed without letting her move. His semen spewed out in four long streaks that went straight down her throat, forcing her to swallow his cum.

Once he was certain that he was done, Ash let Giselle back up. She coughed for a few seconds, and she gasped for air. Ash gave her a few moments of peace; she did deserve them after all. Eventually, she refilled her lungs and she was able to breathe at a normal level once more. She looked up at Ash and saw that he was very proud of himself. She stood up, and she headed for the door, but Ash grabbed her from behind before she could get out.

“You don’t think you’re done yet, do you?” He asked, chuckling.

“Y-yes.” She stammered.

“Oh no you aren’t.” He said running his other hand up her long legs.

Giselle’s body tensed up as she felt Ash’s cold hands rub up and down her legs. He liked the feeling of her skin through the fabric of her tight stockings, but he liked the feeling of it even more the higher he trailed. He crawled his hand further and further up until he was going underneath her skirt. He was expecting to find another article of clothing there, but he was wrong about that.

“No panties, hm? I ought to teach you not go around without any underwear.”

“Please Mr. Ketchum…” She whimpered as he trailed his fingers around her entrance.

He retraced his hand and pushed Giselle her on top of the edge of the table. He pressed her down on her back sent her legs straight up in the air. He folded the skirt higher on herself so that her entrance was accessible, and he positioned himself in front of her. He threw her legs over his shoulders so he could get a better view of the gorgeous girl.

Ash began to pump inside of her while taking her in. Her beautiful brown hair was done into two sets of ponytails, each trailing down the front of her body down to around her belly button. They ran along the side of her B cup breasts that were still hidden under her skirt. Ash didn’t tear off her clothing because he liked seeing her dressed up as an innocent little schoolgirl while he fucked her.

Ash tuned out her screaming as he picked the pace up some more. Knowing very well that she was not a virgin, he had no problem jumping straight to the rough stuff. Giselle’s wetness helped Ash fit his member inside of her. Each thrust forced for Giselle to open up wider than she was used to doing. Her screaming wasn’t a part of the act; she really was feeling a powerful mixture of pain and pleasure, though it was mostly pleasure.

“AH! AHHH! AH!”

Ash had no such mixture; it was completely pleasurable on his end. Her moist pussy was heavenly to him. Ash’s ego soared as he discovered that he must be bigger than any of the guys that she had been with previously because he was a tight fit. Her walls clamped down against him, causing for some serious pleasure.

“OH GOD!!” Giselle didn’t take too long to orgasm

When he felt her cum, Ash decided it was time to change it up. Ash took Giselle off the table and ripped her school skirt off of her. She had no underwear to dispose of so he went ahead and pushed her against the short stool she had been sitting on. Her knees were bent slightly and her arms were crossed laying across the stool. Ash stood behind her and entered her once more.

Ash thought that he was able to penetrate deep before, but this allowed for him to get even further in. He pushed his full length in, directly coming in contact with her g-spot. Her frontal walls provided just enough room for him to maneuver. He quickly built the pace back up to where he had it.

Giselle got even louder as Ash started to pound her once more. He was considerably bigger than any of the other guys that she had solicited herself for, and it caused her core to burn uncontrollably. She closed her eyes, stayed as still as possible, and enjoyed the way his cock filled her all the way up.

Noticing Giselle’s hair flowing down her back, Ash got an idea. He pulled on her pigtails, forcing her to arch her back and raise her head more. This made the already rough sex even rougher. He would yank on her hair every time that pushed forward, letting him reach even deeper than he had been getting.

“OHHH! FUCK! Fuck me just like that! OH! I’m your whore! AHH!” Giselle yelled.

Ash couldn’t imagine a scenario any hotter than the one that he was in right now. He had a beautiful, innocent girl bent in front of him taking his pounding. He could feel his member throbbing down below, begging him to release, but he fought it the best he could. He attempted to ignore it, and concentrated on his performance.

Giselle continued to moan as Ash drilled her. She felt him yank her hair even harder which made it all the more better. When she slept her way to the top of her class, everyone had been gentle with her. Ash was majorly contrasting the style that she was used to, and she loved the change. He took control of the situation right from the beginning which she considered a turn-on.

Ash used his free hand to reach down and squeeze on Giselle’s breast. He knew he was almost done, and he wanted to do a little bit of everything before it was over. He pinched her nipples in order to make her scream some more. It was at this point that Ash could no longer hang on. He told Giselle that he was almost there, and asked her where she wanted it.

“A slut like me is always on the pill. OH GOD!” She barely could finish a normal sentence anymore.

Ash was happy to hear that he need not pull out of her. He gave a few more powerful thrusts before he reached his climax at the same time that Giselle reached hers. Their cum was sent in opposite directions, mixing a little in the process. Ash stayed inside her momentarily, waiting for the high to end before he ended it altogether.

Once he pulled, Giselle stood up on her now wobbly legs. He checked her out for one final time that night. He couldn’t wait to tell Brock that he had managed to score on the girl that they had been admiring. In fact, he thought that his journey could be put on a brief suspension; it wouldn’t hurt to stick around here for a little longer.

“You need to report here at the same time tomorrow if you really want me to keep my mouth shut.” He informed her.

“Yes, Mr. Ketchum” She replied, finishing with a courtsy.


	13. Misconstrue

**Summary for the Chapter:**

> No one ever questioned the Shamouti Prophecy, but Carol discovers a rather important problem

Shamouti Island was in a euphoric frenzy after the dramatic day that had just gone down. Ash Ketchum had just saved the island, and the whole world actually. He had fulfilled the Shamouti Prophecy that foretold his coming to the island, and he had calmed the rage of the legendary birds through the power of Lugia.

A big, wide-spread party was taking place on the island; everybody was there. A banquet was being held in Ash’s honor. There was plenty of delicious food, great music, and the atmosphere was fantastic. Everyone in the room was jubilant, and they were all dancing, eating, and just having a good time.

In a back room behind the stage that was being performed on, Carol sat on a purple, cushiony couch, staring at an old clay tablet. Written in an ancient, foreign language that belonged to the ancestors of the island, the prophecy presented a new puzzle to Carol. She was one of a handful of people on her humble island that actually learned to read the ancient language that was spoken by the inhabitants of the land before them.

The prophecy had been passed down orally for many generations, and no one had read the original words in a great number of years. As she studied it now, Carol realized that the words written on the tablet varied from the words that had been told to the whole community. The differences between what the people had been told and what was written down was not too important, however.

The major points had all come across clearly, such as “The earth shall turn to Ash”, but a few of the minor details were off. These details had no impact on the main point; Ash had still saved the world and all was well for now, but the changes did have an impact on two people on the island. The mistranslation involved the role of the Festival Maiden, which was performed by Carol’s younger sister Melody. Actually, it was as much a misinterpretation as it was that the ending to the prophecy had been chopped off in the oral telling.

Carol left the room almost immediately after her discovery to go track down her sister. She spotted her on the dance floor, smirking as she watched Ash and Misty dance. Carol yanked her on the arm and pulled her over into the room that she had been in just before. The information needed to be communicated as soon as possible.

“What was that for? What are we in here for?” A perturbed Melody asked.

“Well you see… It’s about the prophecy,” She started uneasily, and then continued since there was no interruption, “There has been a misconstruction, and it involves you.”

“Me? What about me? I did my job!” She said, getting defensive.

“I know you did! Or have so far anyway…” Carol trailed off

“Is there something else I need to do?” Melody was getting slightly nervous now.

Carol nodded her head, and briefly searched her brain for the correct way to word her next message.

“As you know, your job was to greet the Chosen One, and perform the sacred ritual, so that he could begin his task.”

“And I did that!” Melody responded, getting defensive again.

“Correct. But the instructions you were given left off the part about what happens to you after the prophecy is fulfilled.” Carol continued to drag on the conversation.

“Wh-what” Melody’s eyes widened in fright.

“The prophecy clearly states that you are to reward the Chosen One after he restores order.” Carol informed her.

“With what, gold? Money?” Melody questioned, wondering where she would get the money from.

“You are… you are supposed to give up your virginity to him.” She said softly, avoiding Melody’s eyes in the process.

“WHAT?!” Melody felt her heart stop at what her older sister had just told her.

“It’s the truth, and I’m terribly sorry for it. But it is clearly written in, and I’m afraid that you will have to go through with it.”

“You aren’t kidding are you?” She asked without much hope at all.

Carol grimly shook her head no. She mumbled something else after that, but Melody was not listening. Her heart was pounding, her mind was racing; she was having a tough time resigning to the whole ordeal. The more she thought about it though, the more relieved she was that it was just Ash. He was a nice guy, and she liked him fairly well. It could have been worse. A lot worse. And she was thankful for that.

She was left alone to her thoughts for a handful of minutes while Carol sought Ash out from the crowd and explained the ordeal to him. Not that Melody knew him too well, but she was pretty sure he would not take the news any better than her. She knew from talking to him and Misty that he must not be much of a ladies man, because he had a nice girl with an obvious crush on him traveling beside him that he had failed to put a move on.

Her thought bubble was popped as she heard an opening and closing of the door to the small room that she was in. Ash had entered, and he looked every bit as nervous as she was. Melody could only imagine the giant mood swing that he must have had when Carol had informed him of the situation. He, along with the rest of the crowd, was in celebration, when he had been told. Now he looked so nervous and worried, for he was as scared as this as she was.

Just as she had when Ash first set foot on Shamouti Island, Melody walked up to him and planted a brief kiss on his cheek. She brought her head back, and gazed into Ash’s eyes. Nerves were evident for both of them, but there was also a sense of resignation on both sides. There was even a tiny twinkle of confidence showing in Melody.

She leaned in once more, and this time she placed her lips softly over his. It took Ash a couple of seconds, but he ended up reciprocating the kiss. Neither of them had ever had a kiss on the lips before, nor did either of them know how nice it would feel. Melody’s lips were soft and smooth, and they lacked any lipstick. Ash could taste a faint trace of fruit on her; was it cherry? Strawberry? Maybe even raspberry? He honestly did not know.

She knew it sounded strange, but to Melody, Ash’s lips were both soft and rough. They were rough in a sense that they were firm, yet they were so soft and caring as well. She threw her arms around his neck, and deepened the kiss a little bit. They both knew that there really was no deep feelings of love involved, but the way that their tongues danced together was romantic nonetheless.

Disappointedly, Melody retracted from the kiss so that she could catch her breath. Once more, she gazed into Ash’s chocolate brown eyes. There had been a change in him; the anxiety and nerves were replaced by excitement. No longer was he anxious as in scared, but now he was anxious in the fact that he seemed to be ready for more. She was glad to see that because she was right there with him.

They crashed their lips together again; this time more fiercely. There was a lot more movement, and it did not take long for Melody to knock her tongue on the gates of Ash’s lips. He let her in eagerly, allowing for their tongues to dance together as their lips had. This kiss was a little less loving, but contained so much more fire and desire.

They began to spin around, and used their hands for exploring just as they were using their tongues. Ash ran his hands up and down her sides, fiddled around with the bottom of her shirt. Melody took it a step a further by unbuttoning his shirt, and bringing it up over his head, which required for brief separation. They wisely used that split second to take in another breath of air.

Even though this was all novel to both of them, it came naturally. They resumed their fiery kiss, and continued roaming their hands. Everything seemed to happen in a blur to Ash; he could hardly keep up with all the action despite the fact that he was the main cause of it. Before he knew it, both he and Melody were half-naked.

He pushed Melody down onto the couch without breaking up the kiss. After he reached back and unclipped her bra, he finally terminated the kiss. He threw her undone bra over by the other clothes, and brought his mouth down on her breasts. She, like him, was in the middle of puberty. She wasn’t flat anymore, nor had she finished growing. Ash figured she was somewhere in transition between A and B cup.

Melody gasped as Ash began to nibble on what was possible the most sensitive spot on her body. If that weren’t enough, he reached down and placed his hand down underneath her wet panties. He rubbed around her entrance, tracing circles on the outside. Her breathing became much quicker as she was getting greatly pleasured.

Not wanting to sit idly and let Ash have his way, Melody reached down and started to work on Ash’s belt and pants. Despite her awkward on angle, she managed to work his belt off of him, and his pants ensued. Ash had refused to stick any of his fingers inside of her, but rather teased her around the edges, and she had had enough of that.

She pushed his head and hand off of her, and flipped him to where he was the one on the bottom. She rubbed her cold hands over his tanned chest, which sent shivers to Ash. Suddenly, Ash’s eyes shot open as he remembered a very important detail. He reached to the floor, and seemed to be looking for something. Melody furrowed her brows in confusion, but her question was answered once she saw what it was.

Ash ripped open a small package, and pulled out a condom. Melody figured that Carol must have supplied him with one, because there was a 0% chance that he just happened to have one. He eyed it funnily, and appeared to be struggling to figure out exactly what to do with it. Melody giggled at the helpless boy, and she grabbed it from him. She put it on for him while his face turned as red as a stop light.

Melody positioned herself over him, and once she felt ready, she lowered herself down onto his rod. She breathed heavily as she let the tip of him penetrate, and she thought about that was going to happen next. Ash patiently waited; he understood that she needed a little prep time for the upcoming pain. After several seconds Melody firmly nodded her head towards Ash. He gave a hard push in response, breaking her hymen.

“AHHHH!” Melody screamed in agony as she lost her virginity.

She gritted her teeth to prevent any further noise-making, and waited for the pain to subside. After what felt like hours but was merely less than half a minute, Melody felt the pain dwindle down to next to nothing. She took a few more deep breaths before she lowered herself back down on Ash’s cock. This time waves of pleasure overtook her rather than waves of pain.

She grinded against him, taking in the fantastic feelings. Despite the fact that Ash would probably be classified under the small size, he still had enough to fill up her virgin clit. Her walls were able to expand far enough to accompany Ash, but it was a nice, tight fit. Ash was blown away by just how tightly he was getting squeezed.

Melody started to slowly slide up and down on him, letting her pussy get filled repetitively. She started to let out soft moans in her happiness. She had never imagined that sex could feel this good even though she had heard some good reviews on the subject. At this point everything else in the world became irrelevant and insignificant. All that mattered was that she was feeling great; that and had managed to save the world, but even that had slipped her head.

“Ohh yes!” Melody didn’t worry about anyone hearing them because the music from the party was so loud.

She had advanced to bouncing up and down on him; the pace increasing steadily and rapidly. The quicker that she went, the better it felt, and her desire grew with each second. Eventually, she became insatiable with what was going on. She ceased her bouncing, and instead hovered right above Ash’s cock.

“Your turn.” She stated simply, letting him take control.

Ash grinned as he started to push himself into her. He spent no amount of time at a slow pace, no, he almost immediately began to pump in and out at a solid pace. Ash began to really check out Melody at this moment. Her long reddish-brown hair was starting to get a little bit sweaty, and his raven black hair was as well. He locked into her beautiful aquamarine eyes that he had started into earlier that same hour. They were truly gorgeous, and he felt he could stare at them for hours. He wondered why she ever wore sunglasses.

He ended up tearing his eyes from hers and he focused back on his task. He placed his hands on her waist and guided her to move down as he shoved up, so as to create maximum pleasure. The amount of friction created was mammoth, and it caused for every inch of both of them to be in pleasure. The part of Ash that wanted him to be “manly” kept him from moaning alongside Melody.

“OH! Oh yeah! Oh yeah! OH!” She let out, delighted.

Melody could only imagine how this would feel if there wasn’t a piece of rubber separating the two of them. She wanted to REALLY feel Ash inside of her. She wanted his meat, not this cheap elastic crap. However, she did not think that the risk of pregnancy was worth the extra bliss that would coincide with it.

Ash bit on his tongue lightly, and bucked his hips to the best of his ability as he felt his release coming. He knew that he could not fend it off, but he had to at least try. He thought that he could get a few more minutes out of himself, but then he felt Melody reach her climax with a loud scream. This caused him to lose it as well, and he shot out his load.

Neither of them had ever experienced anything even close to what their orgasm gave them. It was a final exclamation mark to what was a fantastic scene. Melody climbed up off of him once she had recovered, and she started to dress so she could go back out to the party. Ash peeled off his condom and disposed of it in the trash can.

“It’s a good thing Carol found out about that misconstruction, huh?” Ash asked as he put his jeans back on.

“Don’t pretend like you know what that means,” Melody said with a smirk before walking back out into the main room.


	14. Naive

**Summary for the Chapter:**

> Ash is an amateur in the field of love, so he gets some help from a more experienced person

Ash’s attempt to step forward was thwarted by the slamming of the door right in his face. His mouth was open, but his upcoming sentence was never able to come out. Once again, Misty was pissed off at him. She had now locked herself inside of her room at the Pokémon center. Ash sighed in exasperation and sulked back into the lobby.

He knew that Brock would be in his and Ash’s room if he wanted someone to talk to, but he really didn’t feel like having this conversation with Brock right now. He sat his elbows on the card table and rested his chin on his hands. In his mind he retraced the events of the night, so he could try to see exactly where things had started to go wrong.

Somewhere along the line of his second tour through the Kanto region, Ash managed to ask Misty out. He did it more to end the ceaseless persistence that came from his friends that wanted him to ask her out than actual attraction to her. She said yes with the happiest look that he had ever seen on his tom-boyish friend. Tonight marked six months since they had first become an item.

They had gone out to dinner at a fairly nice restaurant; one where you need not pull out your Sunday best, but you would look out of place if you didn’t wear nice clothes. Dinner had gone by fairly well on Ash’s standards; he had managed to carry a conversation and Misty never got visibly upset. After paying the expensive bill, and leaving a hearty tip, Ash left the establishment feeling pretty happy with himself.

It was right around the time of the sunset, so the couple chose to saunter down a walking path that would require them traveling a little more distance back to their rooms. The walk contained a few silences, but none of which were awkward. Once they were coming within sight of their destination, Misty started acting a little funnier. Ash could tell that she had something on her mind, but she wasn’t voicing her thoughts just yet.

Misty tugged sharply on Ash’s arm before they reached the door. Ash stopped in his tracks to turn and look at her. Even though she had stopped him from entering the building, she did not release her grip on him. He looked at her in confusion while she looked at him with a mix of nerves and anticipation.

“Well, aren’t you going to kiss me?” She asked hopefully

“Wasn’t planning on it.” He said casually and honestly without thinking first.

That stupid comment of his spurned Misty to stomp off to her room without acknowledging Ash’s attempts to stop her and fix his mistake. Ash now realized that he had failed to do anything loving with her in their time as a couple, such as kissing her. He had held her hand on the walk back from dinner, and he considered that a big step, but he knew that Misty must want more than that.

Ash ended his personal flashback, and at this point the Nurse Joy in charge of this center emerged from the operating room; she had just finished working on an injured zubat. She immediately noticed the boy that had checked out a room earlier in the day was out in the lobby. It took no detective work to realize that something was bothering him greatly, and she felt responsible to try and help him out.

“Is something the matter?” Joy asked a dejected Ash.

“Relationship problems.” He answered solemnly.

“I see.”

“You’re a girl, can I ask for your help on something?” He pleaded.

“Of course.”

“I’m not very good with relationship stuff, like you know… kissing, and uh… letting her know I love her and all that.”

“Oh, you haven’t kissed a girl?” She asked, slightly surprised.

“No.” He said, shaking his head slowly.

“Well I feel I ought to help you out.” She said, biting her lip in thought once she finished.

“That’d be nice.”

“How about I teach you?” Joy mentioned, subtly licking her lips.

“Um… ok?” Ash knew he probably wasn’t on the same page as Nurse Joy.

Evidently, Ash and Joy had different ideas on how exactly to teach someone, because Ash was not expecting the upcoming action by Nurse Joy. She, apparently, preferred to teach by example. She leaned down to Ash, who was now sitting up, and pressed her lips against his. She wasn’t surprised when Ash failed to reciprocate; she knew he would be befuddled.

Nurse Joy started to second-guess herself when Ash continued to stay still. For some strange reason, she had expected for him to on board with the idea. If she had actually thought it through, she might have remembered that he did have a girlfriend, that he was naïve in the love department, and there was a solid 20 year age gap between them.

Eventually, Ash ended up pushing his lips back into hers. Nurse Joy would have heaved a sigh of relief if she wasn’t preoccupied with the kiss. She could immediately tell that it was, indeed, Ash’s first kiss. She could sense the uncomfortableness coming from his body, and he wasn’t what anyone would call a good kisser.

She thought that it would be most beneficial if they started over fresh. She pulled away and let Ash collect himself. She could tell that his heartbeat had accelerated greatly, and once it had calmed down, she kissed him once again. Whether it was because he was calmer, or because he had a little more experience now, he had improved tremendously.

She considered this to be passing round one, so she initiated round two. She tilted her head and pressed her lips forward more, deepening the kiss further. Ash handled it pretty well, and he even started to kiss her with more fervor. Suddenly, there was a lot more body movement as the kiss heated up. Nurse Joy moved her hands down onto his body, trying to get him to do the same to her.

His natural instinct appeared to be guiding Ash now; he had bought in on the idea fully, and his hands roamed down to her thighs. She was a fully developed woman, but she wouldn’t be classified as old yet. Ash figured that she was old enough to bear children, and he knew thanks to Brock that guys would refer to her as a MILF. In what Ash thought was the middle of the action, Nurse Joy separated from him.

“And that’s kissing,” Nurse Joy concluded with a pant, “Now there is more I could show you if you like.”

Too horny to think rationally, Ash agreed, “Of course.”

“We’re going to have to move for this lesson.” She informed him.

She led Ash to the back of the Pokémon center; a place that regular trainers never to get to see for themselves. She had wanted to find an unoccupied operating room, but all of them were full. She stomped her foot in frustration, but then she spotted the room at the end of the hall. She immediately scampered over there, and she was glad to see that nobody was in it.

Shutting the door behind them, Joy realized that this was the laundry room, and there were clothes in the washing machine right now. Cursing that there even was a laundry room, she locked the door to make sure that one of her chanseys would not walk in on them. This would have to do, she figured.

Once they were safe and secure, Nurse Joy threw her lips on top Ash’s once more. This time she was able to start removing clothes from him since there was no chance of anybody walking in, like there was at the lobby. She unbuttoned his shirt, but left it on so they wouldn’t have to separate again. She expertly reached down and got rid of his belt with no problem. His dress pants then slid down without a hitch.

Though the kissing was hot, Nurse Joy was ready for something more. She lifted her head away, and then ripped Ash’s only remaining article of clothing off of him. She pushed him onto his knees, confusing Ash because he thought she should be the one on her knees, but she soon let him know why it was reversed. She lifted up the flap of her mini-skirt and revealed her bald crotch.

Before he could try to figure out why she did not have any underwear on, Joy shoved his face into her vagina. Once again, Ash was thrown into an unfamiliar situation, and he was being asked to do something that he never had before. He tentatively opened his mouth, and let his tongue poke its way out. Unsure of what it would taste like, Ash winced before he made contact.

Ash was heavily relieved when it came apparent that it did not actually taste bad. He started to circle his tongue around the edges of her entrance, and mixed it up by leaving kisses everywhere. He still did not exactly know what he was really supposed to do, but he figured he couldn’t be doing that bad of a job.

“Oh stick your tongue in there, honey.” Joy breathed out.

He had been hesitant to do just that, but upon her request, Ash plunged his tongue into her opening. He heard her moan in satisfaction as he explored her with his mouth. He swirled it around, much to her delight. His tongue could only reach so far, yet it still begot plenty of pleasure for Joy.

“Oh give me your cock!” She begged him

She stripped off the apron that all Nurse Joys had to wear along with the short skirt. She pushed so he would lay on his back, and she laid down on top of him. She positioned her slit over his member, and used her hips to lower her lower body with minimal movement from her upper body. She decided that she would take the brunt of the work to start.

She slowly grinded her core against his, creating a heavenly bliss that Ash had never experienced before. Since all he had to do was sit and enjoy it, Ash decided to do something with his dormant hands. He reached up and cupped Joy’s breasts, giving one hand to each. Feeling up a full chest like hers was something that he would not be able to do with a slim Misty.

He played around with her boobs while she started to bounce on his cock. As he squeezed on her C cups, Ash wondered if this was the best feeling he’d ever had. Much to his surprise, it was even nicer than winning a hard fought gym battle. He decided that it was not worth the thought, so he simply enjoyed the sensations. He gave a sharp pinch to her nipples to make her yelp.

Joy decided that she had been in charge for long enough, so she stopped her slow bouncing and left her pussy hovering in the air. Ash, being on the dense side, was unsure why she stopped at first. She cleared her throat in impatience, and then he figured out what she wanted. He slowly pushed his cock up into her clit.

He started to go faster once he became more comfortable with the movements. His squeezes on her breasts became a little less frequent as he focused his thought and energy on his other job now. Wanting to explore her as much as he could, Ash began to shove his full length inside of her. He figured that she must have been with more than a handful of men, and therefore, would not have any problem fitting him in.

The truth was that Nurse Joy had only had sex five times before, and none of those men were significantly larger than the young, developing man that lay underneath her. However, it was no problem for her to fit him in; he was a tight fit, but it wasn’t anything painful. She loved the feeling of him driving his cock all the way inside her.

“Oh yeah baby! You’re getting it!” Joy exclaimed happily.

This instilled more confidence in the amateur, and he began to enter her a little bit rougher. He accompanied that by squeezing on her nipples, making Nurse Joy bite her lip to keep her from screaming. Ash was currently hitting just about every sensitive place that she had. Aching to end her drought of not having an orgasm, Joy let her juices fly on Ash’s next deep thrust.

Ash wanted to change things up now that he had gotten Nurse Joy to finish. He had come up with an idea for a new position, so he pushed Joy off of him and got onto his feet. He pushed her once more after he had gotten up, this time so she bent over the washing machine. He got behind her, and he resumed his thrusting.

“Ooo!” Joy cooed.

The vibrations from the running washing machine stimulating her stomach and chest while Ash went back to work on her pussy. She had thought she was stimulating all of her sensitive points in their previous position, but this one allowed for even more. She had never tried this position, probably because she had never done it in a laundry room before.

Ash rammed his cock repeatedly into Joy’s snatch, bringing her a great joy that she had gone so long without. Her career was one of long hours, and one that pretty effectively kept someone from getting into a serious relationship. She figured since work screwed her out of having sex, then it was alright for her to blow of this hour of work in order to fulfill her sexual needs, while also helping out a naïve young man.

Ash also justified his actions with that thought process. He had never been in a relationship before, so he thought it was unfair of Misty to ask him to do all these things with her that he had no idea how to do. Nurse Joy was being kind enough to teach him, and now he would be able to make her happy. He didn’t know if he was buying his own crap logic or not, but there was no way he was going to stop now and he had to have some kind of reason to ease his conscious.

“Harder! And faster! I can take it!” Joy demanded.

Ash complied, giving her a smack on her butt in the process. He slammed his cock into her with all of the force that he had, and before she even had to time to moan in pleasure, he retracted and forced his way back in. He enjoyed being the one in charge of the moment since he was almost never in charge when it came to his relationship.

He shook Misty out of his mind once more, and he gave another slap on the ass to Joy. He briefly slowed down, giving more sensual shoves for a few moments. He needed a minute to gather his energy, and hopefully buy him a few more minutes. It also provided good contrast, so it felt even better once he picked it back up.

“OH YES!” Joy screamed, not even caring that there were people on the same floor.

Ash knew that these next minutes would be the final run, so he was going to make them the most memorable. He started to give consistent smacks to Joy’s butt while he continued to stick his rod inside of her. He didn’t want to cause any real pain for her; he simply wanted to her feel good everywhere. Boy was it working.

Nurse Joy was on cloud nine because her whole body from her legs up was being pleasured. She felt a climax coming herself, but she hoped to outlast Ash. She knew that a first-timer couldn’t last much longer, but then again, most first timers could not pound her like this. She felt Ash start to rapidly pump in and out of her, and then he finally finished inside of her.

“OH FUCK!” Joy gave one final ecstatic shriek.

Ash started to mentally scold himself right after he pulled out of Nurse Joy. How stupid was he? He had likely just impregnated a woman who was probably twice his age, and he had a girlfriend! He told himself that this had all been a terrible, terrible mistake. Before he could get too far into hating himself, Joy gave him relieving news.

“It’s ok, I take a birth control pill. And now you know how to please your girlfriend.” She said with a smile.

Though he had managed to get out of the whole situation unscathed, Ash realized that he truly was a novice when it came to love. He very nearly made a colossal mistake.


	15. Offset

**Summary for the Chapter:**

> Officer Jenny is willing to let Ash off the hook just this once, but he has to pay her back somehow

Ash was scared out of his mind, sitting in an empty interrogation room. He had simply been chasing a fast running Espeon that he spotted out in the wild when everything went wrong. Apparently the grounds that he had been on were private grounds, and he was trespassing. Not only that, but the Espeon already had an owner, who happened to own that very land.

When that owner spotted Ash sprinting through his land, he called in Officer Jenny to deal with him. She arrived in the middle of a battle that Ash had started against the Espeon. He was trying to weaken it so he could catch; he honestly did not know that it was not a wild Pokémon. Jenny swiftly handcuffed him, having caught him in the act, and brought him back to the police station.

She had led him into an interrogation room, the one that he remained in to this moment, and left, saying that she would return promptly. In the time that he had to think, Ash was scrambling to come up with viable excuses for himself. He was not sure that being oblivious to what he was doing would help or hurt his cause, but he had to make it a point to bring it up with her.

“Are you going to attempt to argue your case, Mr. Ketchum?” She asked when she reentered the room.

“I had no idea! I thought that a saw a wild Pokémon, so I chased it down for a while, and I started to battle it so I could attempt to capture it!” He explained.

“Yes I know. But you trespassed, and attacked an innocent Pokémon.” She informed him.

“I guess I did…” Ash muttered to begin, “But can’t you cut me a little slack? I swear that I had no harmful intentions!” He pleaded.

“It’s not that I don’t believe your story, it’s that I have to obey the law and do my job as a law enforcer.” She said, slightly apologetic.

“I promise I won’t do anything like it again; you just have to help me out just this once!” He begged.

“Well I guess I could cut you a break, but you will owe me something.” She caved in.

“Oh thank you! I’ll do anything!” He said in deep gratification.

Jenny struggled as she tried to think of a way that Ash would be able to re-pay her. After all, she was doing him a huge favor, so it was only fair that he do something big back. She initially thought of community service, but that was too close to a punishment he would have gotten from sentencing. An idea popped into her mind as she eyed Ash up and down; it did not start as her checking him out, but it ended up turning into it.

“You know what?” She asked, “I’ll do something else for you, if you do something special for me.”

“Alright!” Ash said, surprised at his own luck.

Jenny waltzed over to Ash’s side of the table, and rubbed her hand over his crotch. Ash attempted to ignore it, but then she ran her hand up his stomach and undid his top and only two buttons. She scooted her hand underneath the black cotton shirt, and slipped it over his head. Licking her lips at his abs, Jenny set her sights and hands back down to his lower area.

“What is this?” Ash asked bewilderedly.

“It’s a strip search,” She barked, “It’s mandatory.”

Being as dumb as he was, Ash took her for her word. He was curious why he had to be searched since she had agreed to drop the charges against him. Because of this, he gave no response when Officer Jenny pulled his cargo shirts straight down to his ankles. Jenny gave a purr as she rubbed her hands over his package that was only covered by a pair of dark red boxers. She took no time in taking these off as well, and dropping to her knees, she opened her mouth and let his dick inside.

Finally, Ash’s brain was able to comprehend what was actually happening. This was hardly a search; it was the “something else” that Officer Jenny had just mentioned. He was still unable to put two and two and understand what he would was going to be asked to do afterwards. He had had a few blowjobs in his life, but he could tell that this one was going to take the cake. Back when he had dated them, Misty and May had given him a few, but they were not as experienced as the woman in front of him right now was.

Jenny was slowly sliding her mouth up and down on his shaft, swirling her tongue along his member. She knew how to press it against him at just the right pressure; not so light that it was just a tease, but light enough to get his little buddy up and excited. It took no amount of time for his previously limp cock to spring into its full length. Jenny withdrew her lips and stuck out her tongue, giving one long lick that trailed up his phallus.

Once she reached the end, she pressed a light kiss against his tip. She brought her mouth back over the front half of his cock, using her hand to pump up and down on his back half. Ash groaned as her talented tongue went back to work on him. She moved her hand down to cup his balls, and she started sliding further down on his cock. Each time she bobbed back down she took in a little bit more until she had all of him inside her mouth.

“Oh my god!” Ash moaned in intense pleasure.

He felt his balls tighten as his semen built up and was almost to a point where he would have to let it out. He took in a breath and bit his lip in hopes that he could hold out longer. Jenny continued to do her thing without so much as a minor problem. To Ash, it seemed that this must came naturally to her. She had done this enough that her throat was able to open wide enough that a dick could slip its way down there.

Her warm, moist mouth and her delicate, experienced tongue was pleasuring him in a way that he never had been before. Her head bobbed smoothly, letting her tongue give equal attention to every part of him. When she reached down to his base, and his tip started to go down her throat, her throat muscles were able to provide even more hot pleasure to his most sensitive point. Finally, as she came down and swallowed him once more, Ash released his pent up sperm.

The hot, sticky liquid expelled itself and was sent right down Officer Jenny’s throat. Though she never liked it during her first few hook-ups, Jenny had acquired more of a taste for it. She still did not particularly like it, but she was now able to hold back from making any reaction. Instead she stayed still, and she resumed her bobbing right back. She put her tongue back to work, swirling it around his limp cock. With her assistance, it did not take long to get his cock hard again.

“Now you have to put that beast inside me.” She commanded.

Ash was equally as stunned as he was when Jenny put his cock in her mouth. If he was a brighter guy, he would have seen this coming, but he honestly did not. This was his how he was going to offset his debt? It seemed to him that he was gaining something in every aspect of the deal. He guessed that his friends were right; he really was an extremely lucky fellow.

“Yes, Officer.” He complied.

They worked together to get her clothes off as fast as possible. Ash took care of her belt while she removed her hat. Ash moved on to the top part of her uniform and ripped that off for her. She slid the bottom part down to her feet and got rid of it with a strong kick. She was wearing matching, white cotton underwear that Ash tore straight off of her. Ash leaned her over the table and placed his erect penis into her dripping wet pussy.

Ash thought that her mouth had provided a nice, moist place for his rod, but her pussy was even better. It was warm, wet, and tight. He slowly pushed in about half way, soaking it just how great it felt as his cock was clamped down upon. Both of them made scrunched up faces in their pleasure, not caring what they looked like because they could not see each other’s faces.

Ash pulled most of the way back out, and then slowly pushed his way back to the same depth. This was turning out to be one of the most sensual moments that he had ever had. Normally, when he had sex, he jumped straight past the slow part, but today he wanted to take his time. Since he had never mingled around in this stage, he never knew just how good it felt.

He knew that once he pushed in further and began to go faster that there was no turning back, so he kept it steady for as long as his patience would hold. It was slightly teasing, yet it was also had a sense of completion to it. He withheld from vocalizing his happiness, but he could hear Jenny letting some groans emit from herself.

The frontal walls of a vagina are the most sensitive, and Jenny was discovering that through experience right now. His shallow thrusts were driving her crazy; his cock was thicker than anyone who had penetrated her recently, and it caused for him to fit in just right. The way he smoothly pushed into her barrier and rubbed against her walls created a lot of friction.

The amazing feelings seemed to find a way to radiate throughout their whole bodies. It ran all the way from the feet to the head. Subconsciously, Ash started to push more of his cock inside of her. Before he even recognized what he was doing, Ash was stuffing his full length inside of her. The speed of his thrusts also started to increase a rate that was barely even noticeable.

However slow it was, it was still a constant augmentation, and the changes started becoming apparent after a minute or two. He was now giving solid, full pushes into her. Realizing what he had done, Ash abandoned any thoughts of going slowly. He quit the slow build up and rapidly changed into deep thrusts. He grasped Jenny’s hips to get more leverage.

“Oh!” Jenny gasped as the intensity jumped up to a new level.

Ash was pumping at a pace that he was more accustomed to using. He was a little above average as far as size went; nothing astonishing, but better than most. He was considerably bigger than the lone other two guys that she had slept with on the year, so his size seemed a little exaggerated for her. She loved the sensual moment that he had given her a minute ago, but she loved him taking control even more.

Each thrust roughly shook her and sent shockwaves through her body. She likely would have been unable to stay still if it weren’t for Ash holding her hips steady. Her breasts would have likely been bouncing, but instead they pressed up firmly against the table, giving her a little added pleasure. As she continued to feel Ash go to town on her, she was unable to contain herself anymore. She orgasmed with him still pushing into her.

“AHH!” She screamed as she had the best orgasm she had had in a long time.

Halting his pumping briefly, Ash scooped her off the table and pushed her down onto all fours. He got on his knees behind her and picked back up right where he left off. He pushed all the way in, coming in contact with her G spot. After the blowjob that Ash had received from her earlier, he was expecting her to have major experience, and therefore, be on the loose side, but he was wrong. She was just about as tight as his past lovers, only she could take more than they could.

Ash gave a deep groan of pleasure while he kept ramming in and out of Jenny. Not that Ash could explain much of anything, but he had no idea why sex felt so good, or why his whole demeanor changed once he got into that mode. All he knew was that it provided an incomparable joy for him, and all his worries and wants drifted away for the time being.

Getting greedy and craving even more, Jenny raised her ass higher in the air and lowered her head down further. This let Ash enter her easier and a little bit deeper as well. She felt like her whole body was filled with the waves of pleasure that was sent into her with each thrust that Ash made. Her C cup breasts were now bouncing against her body from the powerful movements that were being made.

Ash, with his full cock inside of her, reached down and grabbed her rack. He slowed down his movement so he could focus on groping het tits. By slowing down his thrusting it also helped him regain control so he could postpone his release for even longer. Her boobs fit perfectly into each of his individual hands, and cradled them like the precious possessions that they were. He gave them a full squeeze as he slowly rocked in and out of her.

Changing the speed suddenly once more, Ash withdrew himself ever so slowly, and then hammered himself back in with extreme velocity. He heard her gasp in surprise, but he gave her no time to fully react, and immediately pulled out and repeated the process. He was pounding into her, using the energy that he had recovered while he briefly slowed it down.

“OH FUCK!” She wailed out in ecstasy.

She loved the dramatic style change from soft to rough. There was nothing better for her than to just get down, bend a little bit, lie there, and take it. Her whole body rocketed in movement each time that he smashed into her. The sound of their skin slapping together when he reached as far as he could was music to her ears. The constant noise complimented her persisting shrills.

He didn’t have too great of a view at them, but Ash took great joy in watching her boobs bounce as he fucked her. He could tell that Jenny was having a tough time controlling any part of her body anymore. In fact, Jenny was losing a little bit of control on the inside of her body as well. The constant pummeling was too good for her to hold on forever, and she climaxed with authority.

“OHHH FUCK YESS!” She screamed.

Ash gritted his teeth mightily to hold himself from releasing inside of her. He managed to stop himself, and he flipped Jenny the right way up after he pulled his throbbing cock out of her. He admired her breasts for a fond moment, and shoved his cock right between the wonders. Jenny knew exactly what it was that he wanted, and she pushed her titties in, smothering his cock with them.

Ash slowly rubbed his cock against them, pumping up and down very slowly. Jenny flicked out her tongue and licked at his tip when it emerged from between her breasts and made an appearance. Ash closed his eyes and let out a soft moan. It was like he had exited one section of heaven and headed right next door to another.

Feeling his inevitable release was going to arrive shortly, Ash started rubbing his rod against her firm boobs a little faster. He opened his eyes to take a look, and it was a nice sight. Just seeing his dick covered by those big breasts made him finally lose it. He sprayed his sperm right then, letting it land on her chin and chest. Once his orgasm was over, Ash realized just how tired he was, and he started panting with Jenny.

“You can go,” She told him, “We’re even. Just don’t let me catch you again.”

“Yes Officer.” He said with a little smirk.


	16. Pereigrination

**Summary for the Chapter:**

> What exactly was Misty up to on the day that she left Ash with her sisters?

**Notes for the Chapter:**

> Takes place at the same time as chapter "K"

Slamming the door behind her in irritation, Misty briskly walked away from the Cerulean Gym. Ash kept bugging her to tell him where she was going, and asking to be taken along too, even though she had insisted that she would not reveal any details, and he was not invited. Finally, it came time to leave, and she left without listening to a word of his protest. Granted, she felt bad leaving Ash with her sisters, but he absolutely could not come with her.

First, she had to run a few actual errands from stores that were not local, and she had a meeting that she did not want him involved in. She continued her speed walk until she reached downtown, where she was able to catch a cab. She directed him to take her to the outskirts of Pallet Town, and 15 minutes later, she reached her destination

She paid the man what she considered a ridiculous price, and went on her way. She quickly visited the stores that she had wanted to visit, picking up some medicines and items exclusive to those shops. The small amount of items fit into one plastic bag, and she swung that over her arm as she set out on a short walk out to the Ketchum residence.

Pallet Town did not really have a downtown; it just had plenty of nature and friendly neighbors. She briefly thought about Ash, and wondered if he was surviving her sisters while she strolled along the dirt path. The sun was setting and the scene could not have been more beautiful. If she did not have a place to be she would have loved to have stopped and soaked it all in.

After her short walk, she saw Ash’s childhood house come into view. She walked up the rock path that led to the front door and rapped her fist against the cherry wooden door two times. She prepared a happy and somewhat faked smile so she could give a nice greeting to Delia when she noticed a note sitting on the small table next to the wooden bench. It read:

I’m sorry I had to miss our meeting Misty, but something very important came up. It is about Ash’s father; I can’t give any more details. I tried to call the gym to let you know, but evidently you had already left, and for some reason no one was answering the phone. You can call me later tonight or tomorrow and we can arrange a new time.

Misty’s initial reaction was slight anger, but she knew that Delia was only skipping for a very important event, so she did not stay mad at her. Nonetheless, she was still frustrated, and she ripped the note to release her anger. She stepped off of the porch and started walking back in the opposite direction. As she was walking back along the same dirt road, a large building on the right side caught her eye.

She recognized that she was walking in front of Professor Oak’s lab, and she decided that she would take a stop inside. She had not planned on returning home this soon, so she figured that she could say hello to Tracey and/or Professor Oak, depending on who was there. It had been a long time since she had seen either of them, and the thought of her friends brought a smile back to her face as she approached the front door.

She rang the doorbell knowing that a knock very well might not be heard in the large building. Moments later, the door opened and Misty was surprised to see the door opened by none other than Gary Oak. Gary had given up on Pokémon training, and followed in his grandfather’s footsteps as a researcher. She figured he was here for some help on a project.

“Gary! What are you doing here?” She questioned in slight disbelief.

“Tracey and Gramps took some weekend trip to visit an island chock full of rare Pokémon, and they asked me to look after the Pokémon here while they were gone. As for you, why are you here?” He asked right back.

“Little bit of a long story, but I honestly was just stopping by to say hello.” She answered.

“Well, I know you weren’t expecting me to be here, but you are welcome to still come in if you like.” He said kindly.

“Oh no thanks,” Misty started automatically, but then changing her mind, “Actually, sure. I’ve got some time to kill.”

Gary led Misty to the couch and left her momentarily while he went to the kitchen. He returned with two full glasses of wine, handing one to Misty and keeping the other himself. Misty was not much of a drinker, but since she was having a bit of a rough evening, she accepted the glass. She took a quick sip, and then another. She ended up finishing her glass before Gary even finished half of his.

Gary arched his eyebrows in a comical state of disbelief. She downed the glass a little faster than she should, but he said nothing, and went back in and poured her another glass. They made a little small talk, telling stories of each other’s lives since they had last spoken, which was not that often. Misty finished her second glass just as quickly as the first, and Gary chuckled as he went to give her another refill.

Working on her third glass, Misty began to show some signs of being drunk. Despite the fact that she was sitting, she was managing to sway as she lost balance. Her speech was becoming slurred, and she was beginning to laugh hardly at jokes and stories that really were not that funny. She had never been drunk before, and she was unaware of her predicament.

The alcohol’s affect was becoming larger and more apparent with each passing moment Misty still failed to become cognizant of the fact, but what she did notice was Gary. She had always considered him cute, yet arrogant when they were kids. His ego had not made an appearance on the night so far, and Misty found herself becoming increasingly attracted to the young man that sat opposite of her. She scooted down on the couch to be nearer to him.

Gary did not shy away, but he tried to tell himself that he was misunderstanding the situation. Before he could even attempt to ingrain this thought in his head, Misty brought her right shoulder against his left. This officially made up Gary’s mind, and a smirk found its way onto his face. He, not being connected to life of Misty or Ash much anymore, was unaware of the relationship that they were in, or else he would not have let all of this happen.

Gary turned his face to face hers, and he locked eyes with her. Their heads were about 10 inches apart, and the distance closed at a snail’s pace. Seconds, almost minutes past, and they continued to lean forward ever so slowly with no signs of second guessing. Finally, they closed the full distance and their lips connected together.

The feelings that had caused the pair to create this kiss were not romantic, nor were they emotional. The sole reason behind it was lust, and in Misty’s case, alcohol played a large factor as well. This caused for the kiss to quickly escalate from a soft, beginning kiss, into a fiery, wanting kiss. Hands started roaming as the kiss got hotter.

Misty opened up her lips and let Gary poke his tongue inside. Their tongues mingled as their hands explored each other’s bodies. Fingers found themselves slipping underneath cloth, and lifting up a little bit. They undid all the buttons that they could find, and while taking a short breath, they lifted their shirts over their heads. Gary was now shirtless, and Misty was only a bra away from being topless, and they crashed lips together again.

Gary took small steps backwards, creeping his way towards the bedroom he was sleeping in. Without letting the kiss break off, the two of them found themselves in Gary’s temporary bedroom. Since they were alone there was no need to close the door behind them. Gary lowered Misty onto the bed, still keeping their lips connected. Gary was on top, and they rubbed and interlocked their legs, creating more heat.

The need for air resurfaced again, and cause Gary to pull away his lips. Instead of resuming the kiss right back, he reached down and ripped the blue-white bra off the ginger. Her breasts were but a B cup, but they fit in nicely with the look she had going on. Smiling he brought his hands upon them, but trailed them slowly down her stomach until reaching athletic training shorts.

He pulled the shorts down revealing a wet pair of panties. He started to reach for those too, but before he could, Misty rolled herself so that she was on top, and she yanked off the khaki pants the he was wearing. A bulge was evident as his striped boxers came into view, and that bulge made an appearance as she removed those boxers.

Misty smiled and made a small growl when Gary’s penis came into view. She wrapped her hand around and pumped up and down on him. This got him hard and ready to go in a short amount of time. Keeping one hand on his cock, she used her other to slide her underwear down. She released her hand once she was able to get them off of her.

Gary laid back relaxed on his back with his knees bent. Misty straddled him with one of her legs on the side of his hip and the other between his legs. She slowly lowered herself so that his rod found its way inside of her opening. She only went down by a couple of inches, and she stopped there. She grinded against the fraction of his member that was inside of her, getting heavy clitoral stimulation.

She moved slightly further down, then back up, experimenting around until she found the perfect place. Once she knew that she had found it, she rubbed slowly against his pubic bone. With this seated scissors position it allowed for Misty to be in total control of depth, pace, and pressure exerted. She kept the pace extremely slow, letting the pressure and friction create the heavenly bliss that they did.

Not really used to the role, Gary enjoyed the show while he sat back and let Misty do all the work. He had a nice view of her from this angle; she was turned so that he could admire her front, side and back at the same time. Gary still found it hard to believe the way that the scrawny runt that he had seen at the age of ten had matured into the young woman in front of him.

She had grown multiple inches, now standing at approximately 5’7. If you simply looked at her legs, you might think that she was even taller; they seemed to trail on forever. Despite the vertical growth she managed to maintain her slim figure. Her arms and legs had slight muscle tone from all her swimming, and her stomach was flat as a pancake. Her smooth, silky skin contrasted with her fiery, ginger hair that she had grown out past her shoulders in light waves.

“Oh yeah,” Misty moaned with a deeper voice than usual.

She began to lower herself further down his cock, and she lifted herself back up. She still grinded against him with all of her energy, but now she added in another dimension of sliding part of the way up and down. She never let herself go down all the way, for she wanted to minimize the depth of his penetration right now. She had started a fire in her core, and she did not want to let it get out of control.

Gary’s cock was not as long as Ash’s beast, but what he lacked in length he made up for with his thickness. Considering Ash was her first and only at this point, Misty knew that she had never had anything that thick inside of her before. She was slowly adjusting to him though, expanding her walls further out to provide more room for him. He filled her up nicely, contacting and pleasuring every part of her.

The more time that passed the more adjusted Misty was able to get. Once she felt that she was fully acclimated, she lowered herself down to the base of his dick. Not wanting to get overwhelmed by the new, extra feelings that coursed through her, she gyrated her way back up to where she had been. She stayed there for a tad bit longer, but soon she repeated the process.

Her rubbing and grinding slowly but surely began evaporating and her movements started to resemble bouncing rather than scraping. In spite of the fact that he did not reach as far as Ash did, he still penetrated deep inside of her, and he filled her out a little bit better too. She quickly acquired a rhythm with her hopping, and she changed the angle and rotation of her hips as she went back down to let him touch more places.

Continuously swiveling her hips and pelvis around as she bounced up and down, Misty felt like she was flying. Her whole body was light; her weight seemed to have been sucked out of her with the erotic, pleasant feeling radiating within her. The pleasure she was experiencing had been growing steadily by the minute until finally culminating as she reached an orgasm.

“Ahh!” She gave a loud moan to accompany her release.

She got off of him, letting him choose their next position. Gary pushed her off of the bed, and she laid on the ground on her stomach. He got off the bed as well, and standing up, he lifted her from her torso. He told her to keep her hands on the ground, and he pulled her legs so they wrapped around his waist. He kept his hands wrapped around her waist to provide some support and to give him leverage.

This position required both strength and flexibility, something that they both luckily had. Gary inserted himself inside her, and he was now in possession of the reigns that Misty had relinquished. He pushed himself all the way in, making sure that she could take it. She was, so he pulled out, and tried it again.

He started picking up steam, increasing the frequency of his pushes steadily. He got to the point where he was almost going all out, and he stopped there, leaving something in reserve for later. Gary admired that Misty was able to pull off this position as he kept pumping in and out. It was always nice when a girl could get into a change-up position; one to shake it up from some of the more regular ones.

“Oh yes!” He heard her cry out.

Misty was feeling as loose and free as she ever had. The high from the sex coupled with the high from the wine to make her feel weightless. Any frustrations that she had when she entered the lab were a long way gone now. The logical part of her brain had disappeared with her problems, and she thought of nothing but the pleasure that she was feeling.

Gary almost uttered a light chuckle when he realized who exactly it was that he was doing. Misty, the annoying, tough, scrawny girl that seemed destined for Ash, was happily receiving his cock. He supposed that it was yet another thing that he was able to defeat Ash at. Yes, he always won. Because he was Gary, and Ash was Ash. Gary liked winning, a lot.

He knew that Misty’s arms were probably starting to give out a little because his arms were getting tired as well. He decided that it was time to pull out the last little bit that he had been saving up. He rapidly slammed himself in and out of her, using his hands on her hips to help give him ferocity with each thrust he made.

Misty was getting close to giving out, but she gritted it out because she was loving the action she was getting. Gary filler her up so nicely, not that Ash didn’t either, but he seemed to do it in a different way. With Ash, it was intimate on a couple of different levels. She really did love him, but there was something extra physically satisfying about doing it just to do it.

“Oh my god! YES!” She screamed.

Gary felt Misty orgasm once more, and he used all the power in him not to shoot his load inside of her. He managed to hold it in, and he lowered Misty back down onto the ground. She got herself back onto her knees and placed her hand over his cock. She furiously pumped her hand up and down, squeezing him tightly. She knew that it was coming, and with her assistance, she got him to reach his climax.

“Oh fuck,” He moaned.

He showered Misty’s face with the hot, white liquid that was his cum. She held her mouth wide open, catching any drops that landed in the vicinity. She swallowed the bit that had landed in her mouth, and licked her chin to get the drops that had landed there. She was pretty exhausted, and sleep sounded very tempting, but she knew that she had to hit the road.

She thought about the journey home as she started collected her clothes that sere sprinkled around the room. At that moment, her brain seemed to comprehend what exactly had gone on. She had departed on her peregrination to discuss important things regarding Ash with his mother, yet she ended up sleeping with his arch-rival. He couldn’t find out about this.


	17. Quirky

**Summary for the Chapter:**

> Iris and Ash have a unique type of relationship that is quite difficult to describe

Ash huffed in a mixture of boredom and annoyance as he slouched up against the table. He was being forced to attend a- what was this anyway? He did not bother to listen to the details, but he knew that Cilan was making some sort of speech on one of the plethora of subjects that he was a connoisseur in. He had been placed at one of the front tables with Iris and some other close friends and family of Cilan.

Iris, who was bored as well, only she was a little bit better at keeping it to herself, saw that Ash might make a scene if he was left unattended for much longer. She decided that she needed to entertain him some way before he did something idiotic and embarrassing. An idea hit her in a short amount of time, and she commenced execution of it immediately.

“C’mon Ash,” She beckoned, “Let’s go outside.”

“Alright!” He responded, failing to hold in the enthusiasm he had for ditching the dreadful banquet, or ball, or party, or whatever the heck it was.

They exited out the large, red front doors and took a left turn. They walked in silence for a short difference until a vacant park came into view. Figuring this would do, Iris stopped the two of them there by a bench. She took a seat on it and closed her eyes. Ash was slightly disappointed that this was all she had in mind when she got them out of the boredom trap. He took a seat on the opposite side anyway, knowing that it was better than listening to a speech.

“So,” Ash started, “What do you want to do?”

“Oh, I don’t know. I didn’t really have anything planned.” She answered, cracking her eyes open.

“Oh.” He said dejectedly.

Iris groaned on the inside. Why was this kid so hard to deal with? It was taking care of a baby, only this one could walk, talk, and run. She opened up her eyes all the way now, racking her mind to think of something at least mildly entertaining. Upon opening them, she saw the clear night sky, and that was all she needed.

“How about we just do some star-gazing?” She proposed.

Ash nodded his head in accordance. This wouldn’t be too bad. He cocked his head to get a good view of the stars; he was amazed at just how many of them there were. And there were even more floating around somewhere not visible from space! The subject of stars and space can lead one down a deep train of thought that Ash never bought a ticket for.

Before he got very far into the ride, he felt Iris snuggle her head up against his shoulder. It did not bother him, but he still found it a little bit strange. He said and did nothing to stop her, and then he felt her wrap her arms around his waist, giving him a hug while keeping her head on his shoulders. She broke off of him, possibly sensing some stiffness coming from Ash. She stared into his eyes in a playful, weird kind of way.

Evidently, she was something that she liked, because she scooted closer to him, getting all up in his grill. Her low cut shirt was providing visual assess to her assets, and Ash summoned his self-control to prevent himself from staring at them. He raised his eyes to gaze at her face rather than her chest, and he felt the hot breath being exhaled from her because of the proximity of the two of them. Feeling and hearing her breath, Ash became very aware and self-conscious of his own breath.

He made his breath much shallower in an effort to keep it from making much noise. He must have made some funny face while he was doing this, because Iris giggled at him. She leaned further into him, pushing her chest up against him, and bringing her face directly across from his. Their eyes locked, and their noses were a hair away from touching each other.

Ash’s eyes shot down to avoid the intent gaze from Iris, and they came across two loose mounds. The angle that she positioned herself at gave him a perfect angle to stare at her breasts from above, being able to see everything but the nipple. He forgot that Iris was staring at him, and therefore, was able to easily tell exactly what he was staring at.

“I want you Ashy.” She said with the want clear in her voice.

“And you want me too.” She responded for him.

She had whispered the words right at him, letting the heat that accompanied her voice fall upon his face. Ash gave a small shudder, but either could not come up with words, or he just chose not to respond to it. Since she did not hear a denial, Iris continued pushing forward. She hopped up on top of him, her face still facing his, and she folded her legs on top of each other; her feet were setting on his knees.

She brought her hands to his chest, using one to undo his buttons and the other to rub against him. She purposefully took a little longer than she needed to undo the two button of Ash’s red collared shirt. She used the opening that she created to snake her hand down and rub it against his bare chest. She leaned to his ear once more and asked:

“How about you do this to me?” Sending chills through Ash.

She grabbed his hand, knowing that Ash would have trouble initiating anything, and guided it towards the right direction. Once he was close, she let him go, and Ash reached down her shirt and felt the breasts that he had been staring at. Iris did him another favor by unclipping her bra for him. The low V-cut that let him see her boobs was now the hole that provided his hand assess to her.

He touched them cautiously at first, like anybody who discovers something for the first time. They were a modest B-cup size; a nice size for her curvy body. Ash could not come up with a word to describe them well; they were a little squishy he guessed, yet firm as well. All he knew is that they felt nice, and he wanted to rip her shirt off of her.

He took his hand out of her shirt, simply to pull up on the bottom flap. He pulled it up and over her body, leaving her topless. Iris smiled, knowing that her body had managed to capture the interest of her idiot traveling companion. Before he had the chance to place his hands right back where he had them, Iris pushed her chest into his face, inviting him to use his mouth.

Somehow, Ash picked up on what she was doing, and he opened his mouth, bringing it over her left breast. He sucked on it, a little like a baby he supposed, and moved his tongue in slow circles. After discovering that it tasted fine, he used his tongue like when would on ice cream, frantically licking up, down and all around. He could hear Iris’ breathing deepen as he worked on her breast.

Once he started to get comfortable giving her his oral treatment, he raised up his hand and pressed it upon her other breast. Now multi-tasking, Ash continued to suck on one breast while spooning the other. He caressed it softly, with gentle squeezes every few seconds. He gave a small pinch to her extremely sensitive nipples to get her more riled up.

“Oh!” She could not help but make a little noise.

Feeling that he had run his course on her left, Ash let his hand off of her right boob and placed his mouth over that one. He lifted up his left hand and placed it over the breast that his mouth had just abandoned. He rubbed around it in simple circles with his hand, copying the same movement with his tongue on the other side. He threw in a few squeezes and pinches while he continued his actions for a little bit longer.

Finally, Iris decided that it was her turn to have some fun, and she reached down to his pants. She could feel that he had hardened up, and licked her lips hungrily. Still letting him enjoy a few last moments with her breasts, Iris worked his belt off of him. After she managed to get it off, she tugged his pants down. She followed the same procedure with his boxers, pulling them down slightly. Not all of the way, but enough that he would be assessable.

She knew that a position change would be necessary, so she flipped herself to where her feet hung over the top edge of the bench, her legs laid against his shoulders, her stomach stayed in front of Ash’s face, and her face hung down in front of his crotch. Ash picked up where he left off, sucking and fondling her boobs, while Iris opened up her mouth and took in Ash’s rod. She set one hand on the bench for support, and Ash used his free arm to give her some help as well.

She placed her free hand on the back half of his member while her mouth swallowed in his front half. She tightly gripped him with her hand, and rubbed it up slowly back and forth among the limited range that she had. Since her mouth was only focused on half of him, it was easy to swirl her tongue around every bit of him, but she gave special attention to his tip.

Ash groaned in pleasure, but the noise was muffled into the breast that he was still sucking on. She rocked her head further and further down his shaft, pushing her hand lower to give her the necessary room. She was unable to go all the way down on him; she had not trained herself to that level yet, but she swallowed a solid half-foot of him without as much as a gag.

Iris picked up her mouth, not wanting to give too long of a blowjob, so Ash would not reach an orgasm before the real action even started. She acrobatically flipped herself back around the way that she was earlier. She dropped her pants to the ground, and she let Ash have the honors of getting rid of her underwear. He ripped the purple panties off in a flash, leaving her totally naked. He pulled down his pants and boxers that were still halfway on as well.

She saddled herself into a cowgirl position, letting the tip of Ash’s dick prod her slightly. She wiggled her way a little bit farther down, slowly letting his cock fill her up more. She stopped at about the halfway point, and she grinded against him with all her might. She did all of the moving, all of the work, and she let Ash sit back against the bench and take it in.

Ash now had full permission to do the staring that he had tried to avoid earlier. He looked at her unique purple hair and dark skin with beads of sweat forming along them, her brown, playful eyes that had something different in them, her slim stomach, and her shaking hips. Ash found it strange that the ugly, annoying, kid who had followed him on his journey had become increasingly attractive to him the longer that he knew her.

She slowly bounced up and down on his cock like someone riding on a horse. Her body moved so smoothly up and down against him; she must be a great dancer. The control that she had over her body was impeccable. Swinging around in the forests may have given her some sort of benefits, because she easily seemed within her comfort realm.

“Your turn to work.” She informed him.

She left her body hovering on top of him, but she ceased her movements. Now she was staying still, and Ash started to push forward with his hips. He slowly penetrated inside of her, watching her face to see if and when it got to be too much. He saw her give a cringe that seemed to signify that she was filled up, and he stopped right there. He pulled right back out and stuck it in at the same depth.

He started to go faster once he became familiar with the timing and the rhythm. Feeling confident that he could consistently shove himself in the same place, he thrusted in quicker and quicker. Though it was not entirely intentional, his pushed had a lot more force behind them now that he was going in much faster.

“OH! Oh yeah!” She yelped happily.

Ash’s brain was apparently wired more towards sex than academics, because he did know a few tricks like the way he prepared to pull. He felt himself building up semen, and he heavily backed off of the pace. He reverted back to his initial speed, and he tested her limits once more. This time he could push all of the way inside her without her showing signs of discomfort.

Repeating his past actions, Ash built the tempo back up a slow but steady rate. Once he gained his previous comfort back, he jumped back up to a fast thrusting mode. He heard her start screaming as he put his strength back on out display. A solid thump was created each time that he shoved his cock inside of her.

“OH GOD!” She shrieked.

There was some added dimension of pleasure knowing that they were outside and in public. The park was still abandoned, no one had made an appearance yet, but it was very plausible that someone would. It was different than sex on the beach as well, because at least then you could keep the bathing suits somewhat on and make it less conspicuous. They were fully naked, fully fucking, in a fully public park.

Ash continued powering his cock inside of her, unconcerned about being caught. He felt himself building towards a finish once more, but this time he did not slow down. The event would be over before too long, and they certainly needed to be wrapped up by then. He shoved his dick roughly into her, watching the way it shook her entire body. He heard her screams becoming louder, and with one final thrust, he felt her climax right with him.

“Fuck!” They yelled simultaneously.

Iris expelled her juices down onto his member, and Ash’s cum flew up into her pussy. As much as she would have liked to go for another round, or at least clean Ash off with her mouth, she knew that they had to get back. She dressed herself in a hurry, and started running back towards the auditorium, yelling back at Ash:

“C’mon Ash, we gotta go!” Her playful demeanor present again.

With that, Ash finally came up with the word that he was looking for that described Iris: quirky.


	18. Rejuvenate

**Summary for the Chapter:**

> Candice needs a spark to get her career back on track

**Notes for the Chapter:**

> Takes place during "Double-Time Battle Training"

Candice let a soft, but fake smile, find its way onto her face as she watched Dawn burst up from the table. She went outside, with Zoey following not too far behind, and Brock not far behind her, to work on her contest appeals. Zoey had just earned her way into the Grand Festival, and Dawn was on the verge of qualifying herself. Zoey promised to give her some tips, and Brock just wanted to watch. She saw how talented, and passionate, that the two of them were for their craft.

Candice, for the first time in her young career, could now say that the opposite was true for herself. She had been handing out badges like crazy in the past few months; the latest defeat being an embarrassing one to Ash’s rival Paul. Stuck in a seemingly infinite losing streak, she felt her passion for Pokémon battling begin to dwindle down. It had changed from her love to her job and was no longer both.

She began to question herself; why was she a Gym Leader? There were obviously some more suitable candidates, ones that would not bring embarrassment to the title of Gym Leader. Maybe it was time for her to quit and move on to a career that she was better at. She had fulfilled her childhood dream, but now maybe it was time to let go. She was visibly very troubled, and remembered that Ash was still at the table. She excused herself so she would have some private time.

Walking back to her room, Candice realized that a nice, warm shower could do her a lot of good. She grabbed a few clothes to change into after she was done, and closed herself in the bathroom. She hung up her clothes that would change into, and she started stripping out of her current outfit. Her light blue sweater was the first item to find its way on the floor. Her white undershirt followed next, and soon afterwards, all her clothes lay down on the floor. She took out the pins in her black hair, letting her pigtails fall down on her back.

Candice stepped into the shower and turned the water on. She sighed in her depression as the hot water from the shower provided a small comfort for her. The simple magic behind a shower seemed to solve problems for the young gym leader. It was physically satisfying, warming her body, and also cleared her mind, helping her emotionally as well. She picked up a bar of soap, but she did not use it much at all; she was in here to soothe herself, not to clean herself.

She was deep in thought, so she did not hear the opening and closing of the bathroom door. Partial credit would also go to Ash for being as quiet as he could. Once he was safely inside the restroom he began undressing himself, leaving his pile of clothes right by the one she left. He finished quickly, and tiptoed over towards the shower. He inched the shower curtain open, still staying silent.

He placed one foot in with as much care as he could, managing to stay undetected. Her back was to him, and he could hear her humming a soft tune. He brought his other foot and the rest of his body inside the shower, and inched the curtain back closed. He was pretty surprised that she had not heard him, and he approached her from behind. He reached his arms around her chest, and took a hold of each of her breasts.

“AH!” She yelped, shocked and terrified.

“Shhh… Relax Candice.” Ash spoke softly.

“What are you- How did you- Why are you- What the hell?” She asked

“You know you need this. And I’m sure you want it too.” He added cockily.

“Mhm. Well I guess it couldn’t hurt.” She said softly as he kept rubbing her nipples with his fingers.

“That’s right.” Ash concluded as his smile turned even smugger.

He gave a full squeeze to each of her developing breasts, bringing to pleasure to the both of them. After finishing that he began to rub his hands against her in full circles. He rotating from going clockwise to going counterclockwise every few cycles. Once this ran its course he pulled his hands off and used his index finger and thumb of each hand to gently squeeze against her nipples.

Seeing that they were compatible heights, Ash positioned his member with her main entrance and stuck himself inside of her. Candice’s eyes expanded past their normal levels, but she refrained from letting out a huge gasp. She was stunned motionless, doing nothing to stop Ash from venturing onwards in his bold advancements.

He pushed part of the way in her and stopped there. He inched his head forward and reached around to start kissing her neck. Now triple-tasking, Ash focused his though on giving her a hickey while letting the rest come naturally. He was still lightly penetrating her, and massaging her breasts as well, but now trailing burning kisses around her was his main focus.

“Oh, Ash!” Candice moaned out.

She overcame any awkwardness and surprise that she initially felt, and she fully succumbed to the pleasure. Ash was entertaining in three different ways, and all she had to do to enjoy it was to stand there and let him do it. She never would have expected him to be so smooth, so caring, and so skilled at this, but he was. The childish front that he put on when he was face to face with Pokémon had disappeared now.

The hot water that was rinsing over her body was an afterthought at this point. She now had more effective tools to brining relief and joy to herself. She, like many troubled people, had stepped into the shower to put herself at ease, and to forget about her problems. With Ash’s intrusion, she had very successfully left all her problems at bay. She had entered that very enjoyable mode, the mode that makes time fly, the mode that says “Who cares about the past or the future; all that matters is that you are happy now.”

She felt Ash lift his head up, content with the job that he had done. She only hoped that the red marks would not be noticeable to her friends; she would prefer to keep this between her and Ash. Now that Ash had one less thing to keep his mind on, he put more energy into his thrusting. He started penetrating deeper within her, still not fully entering her though. He kept his arms wrapped around her and his hands covering her breasts. He gave them one more final, soft, sensual squeeze before removing his hands from them.

Ash now pushed his cock’s full length inside of Candice’s tight pussy. He was able to fit inside of her, but it was not as easy as Candice was used to. She did not mind though, heck, it was better that way. He had been slow and gentle with her so far, and she had had time to adjust during that time span. Her vagina was now slightly more accommodating, giving Ash a little more room to work with.

Ash utilized that room, now shoving all of himself in, and slowly increasing his pace. He still kept it slow; he did not want to rush into anything. He knew that right now Candice needed some serious relaxing and calming. He was aiming to provide her with that, while also giving himself a little bit of pleasure as well. He considered himself acting as a good friend, and he thought that it was a win win situation.

“Speed it up, Ash, please!” Candice begged him.

At her request Ash picked up the tempo. He figured she must be able to take it if she asked for it, so he gave it to her. He started to make each push a little bit rougher as well; she may not have asked for it, but faster and harder came together as a duel package as far as Ash was concerned. He heard her moan deeply, and deciding that this position would no longer do, he had Candice bent over so her hands touched the floor, but he could still enter her standing up.

He picked up where he left off once she was able to get securely positioned. The soft sex was a distant thought now that they had made the transition into this mode. Ash pushed all of himself inside her with rough thrusts, and quickly retracted and reentered before Candice could even think about what was happening to her. Candice had handed him the reigns, and Ash took them in a heartbeat.

Candice bent over even further, discovering that Ash could penetrate her even deeper the further that she could been. No one had ever reached this deep before, and she adored the feeling. It was so strange that simply touching that are would produce such happy feelings, but who cares about the science behind it anyway? As stated, she was not in a questioning mood, but rather a “just enjoy it,” mood.

“Oh yes!” She shrieked out.

She bent over a little bit further, as far as she could, and let Ash go to work on her. He pounded inside with all of his might, loving the screams that she let out constantly. He had never fucked a girl like this before, and now he never wanted to fuck a girl in any way but this. He was in control, getting extremely deep penetration inside of a tight pussy.

He did not let up one bit; he had enough energy to last a few more minutes if he needed to. These minutes would not be needed though; Candice needed but a few more seconds. She let Ash smash into a few more times before she lost control of her body and relinquished the most powerful orgasm that she had ever had.

“OH GOD!” She screamed loudly inside the empty house.

She had reached her climax, but she knew that in return for Ash that he would have to aid him in letting him do the same. She dropped down onto her knees, and spun herself around. She swallowed his cock inside of her mouth, letting her tongue flirt around with his member. She was not very experienced in this field, but she was confident that she could get the job done.

She took in as much of him that her dainty mouth could fit, and she wrapped her tongue around all of him, lathering him with her warm, moist saliva. She slowly rocked her head up and down along his shaft, trying to provide attention to as much of him as she was able to. Her bobs were slow, but reached down far on him.

She felt her confidence boost higher as Ash was grunting lightly. She had a sixth sense that he was getting close to releasing. Because of this, she brought her head down to cover all of him. She was gagging something terrible, but she knew that she only had to briefly endure it. Sure enough, this got Ash to go over the edge.

“Fuck!” He exclaimed joyously.

His semen spewed out of his hole and leaked its way down Candice’s throat. Candice tried not to make an ordeal out of swallowing the foul liquid; she was one of many who found it rather repulsive. She was quite the actress, swallowing all of it with a smile on her face. Candice did not take much time to sit and reflect; there was only so much time before the trio outside came back in the house.

She shut off the water and stepped out of the shower. She began to throw on the clothes that she had brought in, and Ash started dressing himself as well. She did not bother to dry or style her hair, both because there was not time and because she did not care. She started to exit the room, but she stopped herself on the way out to give Ash a thanks.

“I really did need that.” She said with a smile, and then she left.

Ash grinned back, knowing that he had put new life into a young, but promising career.


	19. Swingers

**Summary for the Chapter:**

> Dawn wants to spice up her love life, so she sets up a swingers arrangment.

Ash laid back on his bed in stupor. Everything had been normal in his relationship with Dawn, but apparently it was a little bit too normal. Dawn wanted to spice things up, so when May had rejoined the group for a brief little stint during the Wallace Cup, without consulting him, they came up with a special arrangement. He was going to be sleeping with May, but it was hardly cheating, since Dawn had requested it herself. Then once he finished up with her, he would sleep with his girlfriend once more.

Just as he finished reviewing the situation, the door opened and May poked her head in the room. She closed the door and walked up to the bed, but she stopped there. She seemed to be a little unsure of how to start this as well. With a microscopic shrug of the shoulders that Ash may or may not have imagined, she went ahead and began undressing herself.

Ash directed his gaze elsewhere when she first started, but upon remembering what she was doing here in the first place, realized that he had full permission to look. Her orange, sleeveless shirt was lifted over her head, and her tight shorts were pulled down to her feet. She stepped out of them, now only wearing her matching light green underwear. She crawled onto the bed, and sat on her knees right beside Ash.

May started running her hands up and down Ash’s body while he stayed still. It was obvious that he was not yet completely comfortable with his predicament. May had been expecting this beforehand, and she did not let it affect her. She unbuttoned both his shirt and his pants, and lid got rid of both of them. With that, they reached the last intersection in which they could turn around, but May drove right on through.

She pulled off the last item of clothing that Ash had on, leaving him naked. She patiently waited in her current position for Ash to do the same to her. He was going to have to get over the strangeness now if this was going to work. Ash seemed to recognize this as well, because after one final run through in his head, he nodded his head to himself, as if to say that he was ready.

He reached his arm around her waist, and ran his hand up her back until he reached her bra. He unclipped it with ease, freeing her breasts. A small growl escaped from his mouth as he saw her fully developed boobs hanging in front of his face. Something told him that it wasn’t time to play with them just yet, so he forced himself to tear his concentration from them. Instead, he moved his hand down to her panties, and yanked them down.

Now that there were both fully exposed, May pushed Ash onto his back. She crawled on top of him, facing the opposite direction, setting up a sixty-nine position. They had just started, and they were already experimenting with something new to Ash. He stuck his tongue out against her crotch, finally realizing that this idea had some major perks to it.

Ash emitted a small, happy moan as he felt his cock get swallowed by May’s moist mouth. He tried not to let his pleasure from distracting him from his own job. He spread her lips out with his thumbs, opening up the most sensitive part of a woman to him. He lightly touched his tongue right there, driving May a little bit crazy. Not wanting to be a total tease, he cut it out and started to move his tongue all around.

Meanwhile, May was sliding her mouth up and down on his shaft. She wrapped her tongue around his rod, moving it in cooperation with her lips. She was unable to swallow his full member, but she gave a full effort on the portion of him that fit comfortably in her mouth. As her eyes passed over the clock, she suddenly stopped, and crawled up off of Ash. They had set a time limit beforehand, and now it was apparent that they set too short a time.

There was nothing that could be done about that, so they simply had to move on. She rolled herself onto all fours and awaited for Ash to really start things up. After realizing what she wanted, Ash got up onto his knees and positioned himself behind the brunette. He pressed his tip into her, and he slowly pushed himself further and further in. He stopped before he entered in too far, and he pulled most of the way back out. He did the same thing again, only he went slightly less slow this time.

He repeated the same action over and over, each time he went a little bit faster. After a minute or two had passed, he reached a fairly upbeat tempo. He, too, knew that his time with her was waning, so he started to pack more force into each push he made. To be honest, May was not quite as tight as Dawn was. Ash was not surprised by this; one look at her body and it was easy to tell that getting in bed with a man would not require much work.

“More, Ash, give me more!” She pleaded.

He took it up another notch, watching as her big boobs started to have more and more movement. The rougher he got; the more they would bounce. He gripped her hips and forced her back as he went forward. She started to squeal as he pumped in and out of her. He rocketed the speed up to as fast as he could make himself go. As he lost control of his speed, he also lost control of himself, and he reached an orgasm.

May reached one at the same time as him, but hers was a little more forced than his. They were both a little disappointed in the early finish, but they had to move along anyway. There was only another minute before Dawn was supposed to make her appearance with her boyfriend. May dressed herself and left the room without saying a word to the man she just had sex with.

XXX

Briefly afterwards, Dawn made an appearance into the room. She was wearing her everyday attire, except she did not have her white beanie on, and she was missing her pink boots as well. She smiled at the sight of her boyfriend, who did not bother to put his clothes back on, laying out across the bed. She figured that he would be a little bit tired from his fling with May, so she thought that she would warm him back up a little bit.

She hopped on the bed with him, taking no time to get started on her work. She lowered her head, taking his limp cock inside her mouth. Her wet tongue and hot air perked him right back up. She sucked, licked, and blew until he had an erection once more. She could have stopped there if she wanted, but she did not even think about it. She continued to wrap her tongue around his member.

She started bobbing her head along him now that he was back at his full length. She, despite being less experienced than May, was capable of fitting all of him inside her mouth. She brought her head down to the base of his cock, feeling him protrude into her throat. She had trained herself to only give a small gag-reflex from being touched right there. A small gurgle would escape her; loud enough for it to be arousing, but not so loud that it simply sounded disgusting.

Ash, feeling a little more experimental because of the strange occasion, put his hands on the back of her head and took control. It was something that he had always wanted to do, but had never actually tried. He pushed her down, and let her back up, just as she was doing before. She handled it extremely well, so he forced her down roughly and held her there.

He held her head steady and pumped himself in and out of her throat. Amazed that she showed no sign of discomfort, Ash kept doing just the same thing. He felt himself getting close to finishing, so he immediately stopped himself at that point. One more orgasm and he was likely done for the night. He released his hands, and let Dawn trail one last lick along his shaft.

It seemed that Ash just now noticed that Dawn still was dressed, and he planned on fixing that. He tore off the cute mini skirt that she wore on the road, exposing her chest since she had not bothered to wear a bra. She did have the decency to throw on a pair of pink panties, but they did not stay on her for very long. Ash ripped them, and then he dragged her to the edge of the bed.

Once her butt got right up to the edge, he hopped off the bed. He lifted her legs straight up at a ninety degree angle, and he stayed standing. Their pelvises matched up, and Ash started to penetrate her. Her tight, wet pussy welcomed him in happily. He slowly slid himself in, enjoying the fact that he was back with his regular girlfriend. It just felt right this time.

He pumped in and out of her at a constant rhythm. He did not want to speed up too fast, so his pace stayed slow as he pressed into her entrance. He held her legs together, making him feel like a tighter fit. Dawn may not have had the rack that May had, but Ash preferred the fact that she squeezed his cock tighter to that anyway. Her walls clamped down on him in a way that sent him into a state of bliss.

“Oh, fuck!” He groaned out.

He began to quicken his pace without even realizing it. It was a bit of a tendency for him; he just seemed to do it naturally. He pushed in faster and faster, starting to really use some energy. Before long, he was rocketing in and out of her with some powerful thrusts. Dawn had been gasping, but now her gasps were getting louder and louder, eventually turning into screams.

Learning from his experience with May, Ash ceased the quick thrusting, and started rubbing against her clitoris to give him a break. This break allowed for him to get his energy back, and it also kept him from finishing early again. He only stayed in this stage for as long as it was needed; he jumped back to his past pace as soon as he was ready. The quick, unexpected jump surprised the bluenette.

“Oh, Ash!” She exclaimed joyously.

He pounded inside of her with consistent, power-packed thrusts. His pace was rapid; he could not have gone any faster if he wished. He loved hearing Dawn scream for him, and he loved being in control of the sex. The simple, romantic, missionary style sex seemed a little boring to him when he compared it to what they were doing on this night. Ash was starting to fully understand Dawn’s thought process in spicing up their love life a little.

Dawn’s legs blocked a view of her body, but Ash pretty much had her body imagined anyway. Beads of sweat were forming all over his own body from the workout that he was submitting himself to. He was getting tired once more, but this time he chose not to slow down and try to build himself on. Something told him that this needed to be the last phase.

“OH GOD!” Dawn screamed repeatedly.

Ash could have sworn that he heard another girl yelling across the house, but he dismissed the silly thought with a shake of his head. He focused on getting himself to last for another minute or two. It required a lot of willpower and physical power to keep himself going. He was breathing rapidly, for he was running low on oxygen and energy.

If Dawn was enjoying this half as much as he was, which he figured she was, then this turned out to be a great idea for both of them. He had learned multiple things, and there seemed to be a new fire there for the two of them. He gave her everything that he had left, smashing into with his full power. Soon, it Ash simply could not last any longer, and he reached his climax.

“OH YES!” Dawn screamed, having her climax as well.

Ash pulled out, and collapsed back onto the bed next to Dawn. They scooted back up to the pillows and laid down together, closing their eyes. It would not take long for the tired couple to fall asleep in each other’s arms. Laying the way they were, with no clothes, they might end up going at it again when they wake up.

XXX

Brock was astounded, laying in the always vacant guestroom of the Ketchum residence. They had a nicer one that was actually used, but they kept the second as well. Through some deal that Dawn made, he was going to get to sleep with her as some sort of change up from Ash. Not only that, but after May and Ash had their time, he was going to get a turn with May. For all the time he spent chasing after woman, he got handed two on a nice silver platter.

Dawn entered the room with a nervous smile. She hadn’t disclosed the full details of the pan with Ash, and she did not plan on it either. He would probably have said no if she informed him that she was to be sleeping with Brock, so she left that part out when she told him. She walked up to the edge of the bed and then sat on it, wondering how to start this.

She crawled over to Brock, deciding to start it like it was simply normal. She grazed her hand over his crotch, and then tugged on his belt. Brock slipped his shirt off while she got rid of his belt. Once she got it off, she moved on to his pants. She tugged them off along with his boxers in one smooth movement. Once she finished, Brock pulled her skirt down, revealing some not very modest underwear.

They were bright pink with light, tan colored bubbles. They clung to her body nicely, complimenting her fit body. He ripped her bra off and threw it blindly behind him. Her breasts were on the small side, but they were still in a growth spurt. Dawn was expecting her panties to come off next, but out of the blue Brock stood up on the bed and scooped her up in his arms.

He flipped her upside down, hanging her head in front of his cock. He threw her legs over his shoulders, giving her plenty of support. She took his cock in her mouth, heavily aroused by the new position that she being held in. She briefly detached her mouth and spit on his dick, trying to get it wetter. She rubbed it in with her hands, pleasuring him with a quick little hand job, before placing her mouth back over him.

She rocked her head slowly up and down, making sure not to take in more than she could handle. She swallowed most of his shaft with ease, but she did not challenge herself to go all the way down. She had tried doing it with Ash once; it did not turn out very well. She gagged terribly, and she had not tried since. That being said, she managed to do quite a nice on the regions that she did cover.

Brock managed to sense her timidity and reluctance, so he made a decision for her. His arms were wrapped around her waist and back, but he started rocking his hips in her mouth, forcing her to take more of him in. He started with quick, subtle, shallow thrusts, but he gradually increased them. He soon felt himself start to reach the opening edge of her throat, and he heard her to start to choke.

He was expecting this, so he did not cease his activity because of it. He wanted her to learn through experience; he wanted her to power through the discomfort. Dawn had no choice but to accept this, so she tried her best to learn. She widened her throat to the best of her ability, opening her muscles the best that she could. She noticed a slight initial change, but she was still struggling.

Brock halted his pushing to make sure that Dawn had a chance to breathe. He gave her ample time to restore her respiration to normal before he start to resume thrusting. When he did start it back up, he went ahead and pushed himself as far down as he could go. He heard her gag each time that his thrust reached its furthest point forward, but he also noted improvement. Not wanting to overdo it, he finally stopped for good and flipped Dawn back down onto the bed.

She was lying on her back with her knees bent, and her legs were up in the air. Brock got on his knees in front of her and lifted her torso up to the height of his penis. Once he penetrated inside of her; he spread her knees as far apart as he could, opening a hole that gave him a vision of her. He slowly pushed himself further in, staring and admiring her beautiful body.

Her face showed signs of utter happiness as her pussy finally housed a new member. She was unable to immediately detect a loss or gain in size between the two of them. Either way, there was something refreshing about being able to sleep with somebody new. Since she only informed Ash about his end of the deal, and he had no idea about her and Brock, it made it all the more naughty and spicy.

Brock had seen the position in one of his secret magazines, and he knew right when he saw it that he wanted to try it. The separation of the knees provided for a perfect peep hole to admire the girl lying on the bed. Dawn’s face was flawless; she did not use makeup but there was no sign of a blemish. She had high cheek bones and naturally light pink cheeks. Her boobs might not have been big, but there were still boobs, so Brock was still attracted to them.

It may have been due to all the walking that she got in on the road, but her stomach was curved ever so slightly in a sexy way. Her legs were long, flexible, and smooth. She had never developed much of a tan, but her shade of white skin suited her just fine. Brock enjoyed the cool feeling that he got when their skin rubbed against one another.

He was entering her roughly; jabbing himself in with power, but he took plenty of time to bring himself back out. He would let it sit in her at the deepest point for a few moments, and then he would bring himself out inch by slow inch. Once he got back to only having his tip inside of her, he would push back in with a quick, rough pumping motion, which would be greeted with a yelp.

“Oh!” Dawn would cry each time he thrusted in.

Without any kind of hint of his upcoming action, Brock closed her knees in, and he started to furiously pump in and out of the young coordinator. He used the same amount of power that he had been, but he was exiting and entering her at a pace at an exponentially faster rate. By closing her knees, he had also clamped her down more on his cock. Between the tighter fit and the faster pace, Dawn was taken on a thrill ride.

“OH SHIT!” She was unable to contain herself.

She had pretty well lost all control of her body; the only thing that she seemed to be able to control was her voice box. She kept herself from getting too loud because her boyfriend was in the same house as her. There were down in the completed basement, and Ash and May were on the top story in his bedroom, so it was not very likely that anyone would be heard. The basement had walls that muffled sound excellently: perfect for the occasion.

Brock was grunting as he exerted the energy that he had been saving up. Once he amped up the pace; he seemed to have lost himself in his lust and horniness. His mind was empty, but his body was in a fiery pleasure. His thoughts stooped as his subconscious took over the decision-making process. Both he and Dawn had lost control now, so it came as no surprise that they both finished in a matter of seconds.

His mind restored to normal once he reached his orgasm, and he stopped his thrusting. He panted heavily, retracting out of her and flopping onto the bed. He could hear Dawn recovering from the intense action as well. Unbelievable was the word that both of them used to describe what had just occurred. However incredible it was; it was only the beginning. Dawn threw most of her clothes back on, checking the clock to make sure that she was on time for her time with Ash.

They had ended at just the right time, so Dawn left the room and headed upstairs.

XXX

Brock allowed himself to rest and recover from his physical activity for roughly a minute. He started to put his clothes back on, but at that exact moment May walked into the room. He froze with his boxers up one leg; was there really any reason to get dressed? He gave a somewhat nervous look at May, waiting for her to do something.

She walked up to him with a strut in her step. She lightly pressed her hand against his chest, and then she gave a fairly powerful push to get him on his back. She ripped the boxers right back off, leaving him naked while she was fully clothed. She traced her finger along his tanned stomach before removing her shirt. Now shirtless, her bra only did so much to protect her rack from being viewed.

She used the same finger go up her bra, feeling her own breast. Brock could see her moving it in slow, circular motions through the cloth. She removed her hand and inched it up to her bra straps, where she played around with them. She lifted up on them, only to let it fall right back down. She did this a couple of times before moving the show down south.

She pulled her shorts down just far enough for Brock to be able to notice that her underwear matched, but then she fiddled with the shorts, sliding them up and down. Eventually, she slid them all the way down, leaving her only in her underwear. She hopped up on Brock’s lap, gyrating her clothed vagina against his anxious rod.

Having the cloth rub against him was soothing, yet so teasing as well. She smoothly shook her hips in a mesmerizing circle, driving Brock mad. She leaned down over him, her chest falling on top of his, and her face laying just over his. Brock knew that there was a certain unwritten rule that said he was not allowed to do anything, but dear god did he want to.

She pulled herself back up with a flip of her hair. She started to fidget around with her bra again, but this time, she finally let Brock get a peak. She lifted one cup on top of her beast, letting Brock get a solid look at it. She pushed it back down quickly, not wanting to give him too much. She squeezed her melons together, slowly exhaling to agitate the poor man even further.

She horsed around for another minute; there was no time limit this time, so she did not need to sorry about that, before deciding that that was enough. She got off the bed and stood up, pulling Brock up once she was standing. She set her arms at her side and stood there, staring at Brock. After one of those moments that seemed to last longer in real time than it actually does, she pulled him against herself.

Somehow, she had managed to correctly communicate to Brock that he had permission to undress her the rest of the way despite her silence. He got rid of her bra in a snap, quickly moving on to her panties, which he ripped off as fast as possible. He was rearing and ready to go, but May still seemed to be the one in charge. With their bodies still right next to each other, she leaned back against the high, black bedside table.

She noticed some of his clothes were this table, so she brushed everything but his belt off the table. Taking the belt, she hopped up on the table and sent her legs into the air. Brock stepped up to her, waiting to enter her even though their pelvises were at the perfect height. She put one of her on his left shoulder and left the other hanging at his side. Then, she wrapped the belt around his back and held on to the two ends.

Brock began pushing into her, finally alleviating his excitement. May tugged on the belt, making him lean in further and push himself all the way in. She gave what was a mix between a gasp and a moan when he entered his full member. He filled her up better than Ash had earlier. She loosened her grip on the belt to let him withdraw himself, but pulled him back in once she felt that he had gone far enough.

This continued for a couple of minutes until May got tired of working the belt, so she dropped it. She might not have meant for that to be symbolic of her dropping the reigns, but that is what Brock took it as. He thought it was time for him to be in charge. He pulled himself all the way out, surprising May. He picked her up off the table and turned her around. He bent her over the table, picked up the belt, and held her arms behind her back.

He had to keep one hand on the loop made by the belt since it obviously was not as effective as handcuffs would be. He pushed himself all the way inside with a jagged thrust. He pulled out briskly, then pushed his way back in fast as lightning. The sudden role reversal was heavily arousing to the brunette; it had been some time since she had been taken like this.

“OH YES!” She yelled contently.

The table started to shake with all the force being thrown at it. May’s body was being intensely rocked, and there was not much she could do to stop it. Brock was slamming into her so hard from behind that it forced her forward each time that he reached his maximum point. He was screwing her with just about everything he had, but she was taking it pretty well.

He tried to think of a way to take it up another level, so he took his free and combined her separate bunches of hair into his grasp, yanking her head upwards. She screamed even louder as even less of her body was under her control. She was a little worried that their friends would be able to hear them, but that was Brock’s goal. He didn’t care about that. He wanted her to scream, and she was.

“OH GOD! OH YES! AHH!” She yelled as she had an orgasm

Her screams pretty well covered up the sound of skin smacking against skin. Her breasts were bouncing violently against her stomach and chest, while the sound of Brock’s sack stopping him from going any further inside of her also made a solid noise as well. May loved what she was getting, in fact, she wanted more. A funny issue with humans: they always want more.

Alas, Brock could give her no more. He had exhausted any tricks that he knew, and in the meantime, he had exhausted himself. But like an athlete in a championship game, he found a way to keep going past his body’s limits. He continued to hammer in and out of her, relishing the dominant position that he had with such an attractive young lady.

He pulled back even further on her hair, making her crane her head so far that she was staring straight up at the ceiling. He released his one hand from her arms, trusting that the belt would keep them there, and he gave a slap on her butt. He slapped her every other time that he pushed in; he withheld his full strength, not wanting to go too far.

In her kinky mood, May doubted that one could have gone too far, but Brock did not know that. May, having had her boundaries tested well, was now thinking of all the more possibilities that she could try next. Because, she was human, and she could not help but think of how to go further and how to get more. Even with her thoughts of the future, she knew she could not forget this moment.

She had never even thought about doing anything like this with Brock, but now she was thrilled that Dawn had given her the chance. It was a shame that his lines never worked on women, because he had a very nice skillset in bed. She had almost screamed herself hoarse as she felt another orgasm coming her way.

“YESSSS!” She yelled as she climaxed.

Consequently, Brock was unable to go any further, so he let his seed spill out of him. He gave a long groan to accompany the greatest finish that he had ever had. Once he finished unloading himself, he pulled and sat on the bed, closing his eyes. He was so flabbergasted that he could hardly form a complete thought.

The only one that came to mind was; can we do this again sometime?


	20. Tease

**Summary for the Chapter:**

> Ash gets fed up with Jessie teasing him, and he finally decides to do something about it.

To put it shortly, Ash was bitter. His day on the road with his friends had gone downhill in a hurry. They were only an hour out of the next town when Team Rocket made their usual, disruptive, annoying appearance. Unfortunately, this time they had been fairly successful in their attempt. With some help from expensive machinery, and a little bit of luck, they captured Pikachu.

Ash managed to grab onto the edge of the passenger section of their balloon before they could take off in escape. He reached for his poke balls, and he released the first one that he found. Luckily for him, it was a flying type, Noctowl. He ordered it to use wing attack immediately, which rocked the balloon. Unfortunately, it rocked the balloon too hard, and he lost his grip. The gust was mighty powerful, and Jessie lost her balance, falling over the edge as well.

They had not managed to reach a very great altitude, so the fall was nothing that could have killed them, but it was pretty lucky that neither of them broke any bones. Noctowl was too focused on his business to even notice that his trainer had just fallen off. He kept attacking the balloon, and followed it once that he got it out of the air. Brock went after Noctowl and Pikachu, leaving Misty to try and find Ash.

After twenty minutes, it became apparent that Misty had gotten herself lost in her quest, so Ash was stuck with Jessie. It was not the first time that the two groups had gotten split up; it happened multiple times due to Team Rocket’s shenanigans. Nevertheless, Ash was stuck with Jessie, and he had lost all of his friends, including Pikachu. Needless to say, he was a little ticked off.

He looked over at Jessie with disgust. She was wearing the same outfit that she wore every day. She had on her white shirt that cut off above her midriff with long black sleeves covering her arms. Her shirt even had been cut into from the bottom, showing black material underneath that Ash assumed was a sports bra. She had a small white bottom that looked like it belonged to a skirt, and long black socks that covered most of her legs. It was a rather slutty outfit in Ash’s opinion.

In fact, it seemed to him that Jessie was toying with him a lot of the time. Throughout his journey she had thrown him some winks, stretched out in front of him, and put her body in some unnatural positions. Just as he was thinking that, Jessie bent over right in front of his face to pick something up. He could not tell what it was because her ass pretty well blocked her view. He felt himself growing hard as her clothes scooted up and her skin became more exposed.

She wiggled it around a little bit for him, then stood up and looked at him with a small smirk. This event set him over the edge; she was teasing him. She was fully aware of what she was doing, and she found it amusing. Well it certainly was not amusing to him, and he was going to let her have it next time she pulled some of her funny business.

He did not have to wait long for Jessie to mess with him again. As he reached for some fruit on a low hanging branch, he felt her graze her hand against his crotch. He maybe would have tolerated it if it was a quick brush, but she left it there for an extended period of time. He had made up his mind beforehand, so this time he did not just let her have her way.

He clasped his hand down on hers, forcing her to keep it there. Then he used his other hand to unzip his pants. He heard Jessie gasp as his pants loosened. He lifted her hand briefly so he could work them down a little bit, leaving him only contained by his boxers. He forced her to rub against his member, now giving her a much better feel for him.

“You’ve been asking for him Jessie, so you’re going to get him.” He said, referring to his cock.

“What- I don’t- no no no.” She said, backpedalling from her previous actions.

“Don’t try to back out of it.” He told her.

She was still stammering, but he did not care. He let her hand go once more, this time to pull down his boxers and unveil his rod. He then bent her over and shoved her mouth over his very hard boner. He stayed standing, using both of his hands to shove Jessie’s head down on his beast. He took no time at all to force her to swallow all of him.

Jessie was stunned at Ash’s size; he was large both in length and thickness. She had never expected that her fooling around would ever lead her into this, and she never expected for Ash to be so big. He put James to shame, but that wasn’t much of an achievement anyway. Still, he filled her mouth and then some. She did not think it was physically possible that he could fit all of himself in her mouth, but he was.

She tried to breathe through her nose as her mouth was being forced to slide up and down on his dick. Even that was a tough task because his monster found itself sticking down her throat, blocking the air passageway to her nose and her mouth. Because of this, she tried to take big breaths when her head came up for a brief second, during which she had an opportunity to get some air.

Ash felt major satisfaction in having his cock moistened by Jessie’s mouth. It was sweet revenge for all the angst she caused him, and the more he thought about, he was taking out a little anger that other females like Misty caused him. It seemed that every girl he knew was messing with his hormones. If he was in a right state of mind, he might realize that he was exaggerating everything a bit, but he was unable to process thoughts normally.

He was mad, and this was his way of getting it out of his system. Hearing Jessie gag and struggle for air was music to his troubled ears. He started to pump his hips forward each time that he used his hands to force her down. He dropped one of his hand to his side, and he grabbed a bundle of her hair in the one that he left up.

He gripped her dark red hair firmly, holding her head in steady place. Then he continued to push his cock in and out of her mouth. He pushed himself in as far as he could and left it there momentarily. He chuckled as her mouth expanded and he could see her losing oxygen. Her struggle was amusing to him; it was the exact opposite of the situation just minutes ago.

Ash smiled, looking around to make sure no one was around. He was unable to see anybody, and Jessie was hardly in a position to where she could try for help. He resumed his pumping; his throbbing cock close to releasing its contents. Her mouth felt heavenly, and there was something even nicer about it, knowing that she was not on board with the idea.

Jessie was unbelievably uncomfortable in her helpless position. She simply couldn’t handle all the cock that was forcing its way inside her mouth. Her uvula was taking a pounding, and she found breathing, what should be a simple task, to be nearly impossible. Just as she thought she was going to black out, Ash forced her down once more with one final thrust up, unloading his semen into her mouth.

Ash held her head steady as he released a full load into her. He waited for every last drop to find its way out, and then left his still firm cock lodged in anyway. Jessie choked violently with his massive cock still preventing her from breathing, and now she had a large amount of his cum to keep in her mouth as well. Ash let it slowly leak out of her mouth, keeping his dick in her throat the whole time. It seemed to take forever for all of it to clear out, but eventually it did and Ash let his grip grow lose.

Jessie collapsed to the ground and coughed loudly once she was free. When she finally brought her eyes up to look at Ash, she realized that she was strangely turned on. Even though he had just done that too her without her consent, and though it was a bit painful, she seemed to like it deep down. So instead of running away in terror and fear, she stayed right where she was.

Ash was surprised by the look she gave him; it seemed to tell him that she wanted more. That suited him just fine, because he was not ready to be done either. He pulled her up and ripped her shirt open, causing her big breasts to flop out into the open. Ash was slightly surprised at just how big they were, but he withheld himself from doing anything with them. Instead he went down to her bottom and pulled off the rest of her outfit.

Ash pulled his pants and boxers the rest of the way off, so he could have more freedom of movement. He leaned her forward before he entered himself in her from behind. He moaned loudly as her warm, wet pussy devoured his penis. Her mouth felt fantastic, yet this felt even better. He slid himself in slowly, marveling at just how great it felt. The feeling was so soothing that it could have calmed him down, but that wasn’t what he wanted to do.

He wanted to stay mad and in control; there was nothing romantic about this. He grasped her hair again and slammed into her powerfully. Her pussy was incredibly tight, clenching onto his big dick. He kept using strong thrusts, picking up speed at a solid rate. Jessie was unable to hold in her screams, no matter how hard that she tried. His cock filled her and then some, stretching her walls out to distances that they never had been to before.

She held onto a tree to keep herself from falling over, and Ash holding her helped her keep her balance too. Her screams died down into long, articulate moans since she did not really have the power to yell. It sounds silly, but she was so roughed up that screaming was not even possible. Soon, as she was still attempting to get accustomed to her treatment, Ash started to spank her.

He slapped her right cheek each time that he slammed himself inside her pussy. It was only several seconds after that when Jessie lost control of herself and climaxed with Ash still pumping away. Ash did nothing to acknowledge that she orgasmed; he only switched hands, now slapping her left cheek. He pulled back harder on her hair, prompting Jessie to look back at him.

She was amazed at his ability; he was pretty young to be this good. He was pumping into her with reckless abandon; he hardly even seemed to be thinking about he was doing. It all came naturally to him, which was hardly surprising given his unnatural “gift” that he had been blessed with. He hammered into her repeatedly, each push the same as the last, but each one seeming greater than the last.

He had slapped her cheeks evenly, both of them now displaying the same shade of pink. He ended up abandoning the spanking and focused on speeding up his thrusts. He pulled harder on her hair as he started to rapidly move his hips. He had reached a speed that made his dick look like a blur as it rocketed in and out of her slowly expanding pussy. His thick cock had continually stretched her throughout the sex, and his length reached depths that she had never dreamed would be touched.

Ash watched as Jessie’s breasts bounced wildly, her body shaking like crazy. They were larger than any that he had ever seen; they were mesmerizing to watch. He loved to watch Jessie’s body shake helplessly due to his actions. He heard give an extended, loud, moan as she had another full orgasm. Her pussy contracted down even more on his members, yet miraculously he kept himself from spilling his seed.

He pulled out of her, letting her to sink to the ground in her exhaustion. He looked at her breasts again in wonder, deciding to do something about it now. He pulled Jessie up to her knees and laid across his back. His boner was sticking straight up, and brought her breasts over to engulf it. He then laid his hands behind his head and let Jessie take charge.

She squeezed her breasts in, rubbing them against his rod. The heavenly feeling that accompanied touching her balls of fat was a bit strange: inexplicable. They were so soft, yet firm, and large as well. She pressed them in, and slid them up and down his member, earning groans of approval from the raven haired man that had been the one in control until just now.

Ash started grinding his hips, pushing his dick more into Jessie’s mounds. They were big enough to cover him completely, almost acting like a blanket. Ash’s smile grew even larger as he remembered the roller coaster of a day that he had had. It started off as a solid day, then seemed to take a big turn for the worse, only to escalate back to the top with his current situation.

His cock was about to burst, and had been so for quite some time, but he kept control for as long as he could will himself to do so. Her squeezing and his pushing created an amazing electricity that transmitted itself across his whole body. He was putting forth minimal effort but getting plenty of return from that little work. He felt like he was flying free in the endless sky, enjoying the air beneath his wings.

His heaven finally came to a climax when he reached one of his own, shooting his sperm into the air. Jessie stuck her tongue out, catching any droplets in that range, letting the rest collect on her boobs. After his second major orgasm of the day, it was an understatement to say that Ash was spent. His hard cock finally fell limp after disposing of two large loads of cum.

Jessie fell backwards onto her back, mimicking Ash’s position. She had been treated way rougher than she was used to, and her body was beyond tired. A long nap sounded so good to her that she did not even bother to put any clothes back on. Hopefully, for both of them, they would not be found by their friends in their current positions.

Before Jessie fell asleep, Ash spoke to her for the first time since he initiated the sex.

“Don’t fucking tease me, ok?”


	21. Ubiquitous

**Summary for the Chapter:**

> Tracey and Daisy have taken it to the next level physically, but one afternoon, they take the emotional step as well.

Daisy held a brown paper bag of groceries in one arm as she searched for her keys with her other. The golden haired gym leader fumbled through the multiple keys on the key chain before finally finding the one that would unlock the door. She slipped it into the keyhole, and twisted it to the right, listening for the click that would notify her that the door was unlocked.

She set the groceries on the kitchen counter and headed for the stairs. She ascended them with the assistance of the railing, turning left once she reached the top, advancing toward her room. She stepped inside of it, and unsuspectedly walked into the bathroom. A shriek came from her lips as she spotted Tracey standing in her bathroom, holding a wrench.

“What are you doing here?” She asked aghast, just then remembering that her door was unlocked and someone had to have been in the gym.

“Well, you said your toilet was broken, so I came over to take a look like you asked.” He responded bashfully.

“I said if you got a chance some weekend, not right this minute.” She said, chuckling at his willingness to come over.

The more she thought about it, Tracey was always over at the gym. He was a nice handyman, fixing a bunch of little, and a few big things. It did not seem to bother him though; he was always happy to come over. In fact, sometimes it seemed that he came over for any little excuse. Daisy, being a little conceited, assumed that he must want to spend time with her, now that she put together how much he enjoyed coming over.

“You are a really sweet guy, Tracey.” She acknowledged.

A light stripe of red appeared along Tracey’s cheek; he blushed at just about any compliment he got, but even more when they came from cute girls. Despite the fact that he and Daisy were openly dating, he was still “cutely awkward” according to Daisy when it came to expressing their fondness for one another. He had never had a girlfriend before her, even at his age of 21, so it was a new experience, and he was still learning.

“But why don’t you spend a little time with me?” She asked sweetly.

“Oh yeah, sure.” He responded, setting his tools down.

He stepped toward her and flashed her a smile. He was not really sure what it was that she wanted to do, and he was hoping that she would end the silence that fell upon them after he last spoke. Just as he hoped, Daisy wrapped her arms around him and pulled him next to her. He put his arms around her back as well, completing the hug. He liked the way that she fit into his arms.

Her green eyes lit up and sparkled as they locked with his brown ones. There is no doubt that the eyes provide some sort of passageway to the soul; anyone who has truly looked someone in the eye can attest to that. Something clicked when their eyes connected, and Daisy leaned her head in for a kiss. Their lips met softly and stayed together for a few brief moments.

They parted their lips, but their heads did not travel far away. They looked into each other’s eyes again, spawning Daisy to lean in for another kiss. She pressed her lips against his harder this time, and she did not pull away after a few seconds. She crept her tongue out of her mouth, pressing it at the gates of Tracey’s mouth. He reacted a little slowly, but he opened up his mouth and let their tongues mingle.

Daisy’s hands moved up to his neck and she leaned further in, deepening what was now a make-out session. Daisy had mastered the art of taking in small breaths with her nose, and when an opportunity presented itself, her mouth, while she was kissing. She never needed to break a kiss to get some air. Tracey, on the other hand, was not so experienced. He had to pull away for a second to replenish his air supply, but Daisy pulled him back in before any amount of time passed.

Daisy started to take small steps backwards, yet kept the kiss going. Tracey followed her, not that he had much choice anyway, as she had her arms around his neck and was pulling him with her. She took her time so that it did not take away from the kiss, but eventually she backed them up back into the main part of the bedroom, next to her bed. She turned them around and threw him onto the bed, falling on top of him when she did so.

This time Daisy did break away, but it was not because she needed to breathe. She ran her fingers along his chest and collar as he panted, taking advantage of his chance to catch his breath. She unbuttoned his polo without any resistance, and he responded by ripping off the pink sweater that she wore just about everywhere. Daisy reattached her lips to his at this point.

Restarting the fiery kiss, Daisy placed her hand underneath the fabric of Tracey’s shirt and pulled up on it. In a flash she managed to separate their lips and fling the shirt of his body. Before Tracey could even realize that their lips parted, they joined once more. Impressed by her move, Tracey wanted to emulate her. He pulled her dark blue shirt up as far as he could with their lips connected. He pulled away from her and tried to fling the shirt away in just the same way, but he was not as successful.

Her shirt got hung up on her shoulders, ruining the smoothness that he was attempting to get. He did not let it get to him though, he peeled the shirt off of her and pressed his lips back onto hers. A new challenge presented itself this time: her bra. His hands were already on her back, so he started to move them around in search of the hook. He found it quickly, and he fumbled with is, desperately trying to get it off without any trouble and embarrassment.

It took him three or four attempts, but he got it off without making a scene or anything. They had succeeded in getting each other topless, and they continued to poke their tongues at each other. Daisy began rubbing her legs against his, creating some more electricity. The currents coursed through the couple’s bodies, causing an ineffable joy for them.

Finally, the wait got to be too much for Daisy, and she broke apart from Tracey to get rid of his clothing. She ripped his khakis off, and his blue and black underwear was not visible for very long before it, too, was disposed of. Being fully naked reminded Tracey of the first time that Daisy saw him naked and how bashful he was. He was much more comfortable with it this time.

Tracey returned the favor to his girlfriend, taking her white shorts without hesitation. Next came her purple panties, which became the last addition to the pile of clothes that had accumulated. Now that they were both fully exposed, Tracey performed an out of character action and was the first one to act. He brought his head down to her crotch and placed his mouth at her vagina.

He stuck his tongue out and lapped at her entrance. Her pussy was already wet, proving Daisy was getting pretty hungry for sex, but unfortunately for her, she would have to wait a little. He licked around her outside at first, then moved on her inner depths. His tongue could not reach far inside, but it need not to. The shallow reach of his tongue was plenty enough to get her going.

“Oh! Oh god!” She would moan.

He was toying with what is probably the most sensitive part of a lady, and it drove her body mad. She bucked her hips in a natural reaction. She seemed to lose control of the lower half of her body while Tracey was orally pleasing her. The coolness of his tongue helped to calm down the burning fire that had started down in her core in some ways.

Tracey started to flick his tongue back and forth quickly, listening to Daisy moan in a higher pitch as well as more often. He could feel her body shaking, and he could sense that an orgasm was not far away. Not trying to be a jerk, but rather to save up for a bigger finale, Tracey stopped his action completely and left Daisy hanging. She whimpered in protest, but she did not say anything.

Tracey then got back on his knees, and Daisy sat up and joined him there. She looked down at his member, and saw that he was not quite ready. She placed her cool, creamy hand around his dick, and stroked it slowly back and forth. Tracey immediately reacted to her soft touch. It was incredibly arousing, and he was fully erect in no time.

Daisy brought her other hand down and placed it behind the one she was already using. She found a way to grip him tightly, yet softly as well. Tracey was given a little bit of a taste of his own medicine as Daisy ran her hands up and down his rod, only to stop when he felt himself building up. It was a little bit frustrating, but he did know that it was for the best.

Moving on to the next level, the two laid down on the soft bed in a simple missionary position. Tracey reached over to the bedside table and pulled a condom out of the drawer. He put it on before continuing. He inched his cock forward slowly, stopping once he began to prod her. He heard Daisy let out a mix between a moan and a groan as she was anxious for more. He shook his hips a little bit, barely penetrating her, but dancing around instead. He was postponing his entrance as long as he could; he wanted to hear her whine.

“Traceyy!” She said pleadingly.

He chuckled, and then gave in and plunged himself into her pussy. He slammed his full cock into her, knowing plenty well that she could take it alright. He left it there without pulling out, repeating his actions from seconds ago. He grinded his hips, making his cock dance around some more, but this time, he was inside of her. The temperature seemed to be over 100 degrees; their proximity begetting all the warmth.

Needless to say, it was not an uncomfortable heat, but rather a relaxing, soothing, and all around pleasing like one you would get in a hot spring. Tracey slowly pulled his hips backwards, pulling himself out of her, before pushing himself in with a quick, sharp thrust. He kept himself there, circling his hips yet again. He repeated this process multiple times; pulling out slowly, and pushing in fast.

“Oh, Tracey!” Daisy moaned out.

She was breathing heavily, enjoying the sensuality that came from Tracey’s movements. She was more used to rough, meaningless sex, so the change was refreshing on its own. Daisy, who was often grouped in with her sisters as dumb, was a little bit more intelligent than she was given credit for. She understood that the emotional connection between her and Tracey helped add another dimension to the sexual intercourse.

It was more meaningful; there was passion and what Daisy was starting to think was love. They were, after all, making love. Neither of them had said it out loud yet, but for the first time, Daisy thought that she was in love with Tracey. It had a strange ring when she said it to herself in her head, yet it still seemed right. Tracey and Daisy. It even rhymed.

Strangely enough, similar thoughts were running through Tracey’s mind at the same time. While the missionary position can be viewed as vanilla or boring to some, it seemed perfect to him for the occasion. He admired her beautiful body, and when he stared at her face, it all clicked. It took one final peak into her eyes, into her soul, but Tracey knew at the moment that he was in love.

Once one is in love, appearance becomes irrelevant. Tracey, like all men, considered Daisy to be a very beautiful woman beforehand, but now he did even more so. It was like he was looking past her perfect body, looking at something more, seeing the heart and soul of the woman who had captivated his heart. It felt like he was looking at a different person now.

Tracey gradually cut out eh slow exit that he was using, picking up the overall tempo. It was still very much on the slow side, but that did not take away from the bliss. Tracey leaned in and kissed Daisy once more as he continued to slowly push his cock in and out of her. Their lips met, fitting together perfectly, and they both sent their love through it.

They started to press harder against each other, making the kiss more passionate. It turned into a little “I love you more contest” as the kiss started to mean more and more to each of them. Tracey had to break away before too long, cursing himself for not being able to breathe like Daisy could. He did not kiss her again, however, because he had already gotten his message across. Daisy and he both had said what they needed to say in that very kiss.

The heat in the room increased steadily, almost in proportion to the speed that Tracey was building up. The slow augmentation had suddenly quickened; it was like the last mile of a marathon, when everything speeds up dramatically because the end is near. He was soon pumping into her at a fast pace, causing for the buildup of more pleasure.

“OH! AH! AH!” Daisy was letting out high pitched squeals.

The increase in his speed stopped; it seemed he had reached the peak. Everything, including the pleasure, had reached a climax, and fittingly, Tracey and Daisy reached their physical climax within a minute as well. They both let out a long, lengthy moan as they expelled their juices from their body. They breathed heavily, looking at each other in full happiness after their finish.

With the events that transpired since she returned home, Daisy now knew that Tracey would be there for her, whenever she needed him. Both physically, for fix it jobs, and more importantly, emotionally.


	22. Validate

**Summary for the Chapter:**

> The Sensational Sisters hear a rumor about Gary and need to see if it is or true or not.

It had been a few weeks since the evening that the Sensational Sisters managed to seduce Ash, despite him being in a relationship. It had been a very pleasant experience for the three of them; in fact, there had been a few dreams about it. There was no question that they wanted to do it again, but they couldn’t. There was almost no way that they could convince Ash, and even if they could, they would have to feel guilty for sleeping with their little sister’s boyfriend.

They had not talked about it amongst themselves yet, but they were all looking for some way around their predicament. They had all suffered through a dry spell, and they were looking for some satisfying sex with no strings attached. Hitting up some clubs was always an option, but the men there were never anything to remember. They needed somewhere, or someone, else to turn to.

The three of them all happened to be pondering over the same predicament as the all sat at the table enjoying lunch. Lily finished her sandwich, but stayed at her place at the table. She thought that she had a solution, but she was debating in her head whether or no she should speak about what was on her mind. She ended up deciding to verbalize her idea to her sisters.

“Girls, would you be interested in having another fling together?” She asked, knowing the answer.

Violet and Daisy, her sisters, looked at each other with a smirk, conveying that the answer was a yes.

“Well, I have a guy in mind.” She continued, taking their gestures as a yes.

“Who?” Her sisters asked in tandem

“Gary Oak.” She said, glancing back and forth between her sisters to gauge their reactions.

Lily had heard a rumor that Gary was a man that looked for sex rather than commitment and relationships, which was exactly what they were looking for. The second part of that rumor is that he was quite skilled in bed. It seemed that he fit their criteria to a T, and her sisters agreed with her. Apparently, they had heard the same rumors themselves.

XXX

Gary yawned, stretched on his leather couch. He picked up the TV remote and flipped through the channels mindlessly. He finally put the remote down when he reached the sports channel. He closed his eyes and half listened; he did not much of any interest in what was on anyway. Just as he got comfortable, and he was about to take a snooze, he heard the loud ringtone of the telephone go off.

He groaned in protest, debating whether or not he should answer it. He opened his eyes, but he did not get up from his spot on the couch. He finally picked himself up after a couple of seconds, giving up hope that the ringing would stop. He trudged his feet along the carpet, taking a much longer time to talk into the kitchen than he needed to. Once he reached the phone he picked it up and mumbled out a greeting.

“Gary?” The voice on the other end asked.

“Speaking.”

“It’s Lily, from the Cerulean Gym. I’m one of the Sensational Sisters.”

“Yeah, I know who you are.” He said with a smile, remembering watching her and her sisters perform.

“We have a bit of a problem over here at the gym, and we were hoping you could help us out.”

“Sure, I will be right over.”

“Great!” Lily responded before hanging up the phone.

XXX

Gary had hopped straight into his sports car and headed for Cerulean City at an above the speed limit pace. He reached the city in 15 minutes, and after another 5, he managed to find the gym. He walked up to the doors coolly and calmly, and he rapped against the door twice. He put on his signature smug smile as he awaited the girls to answer the door. He heard an immediate scuffling of feat, and then Violet opened the doors.

“Hey! Come on in!” She greeted him.

He smiled back and followed her into the massive gym. The thought just occurred to him that nobody had mentioned to him what exactly the problem was, nor how he was supposed to fix it. He did not think much of it, but he found it a little bit odd. He scaled the stairs behind Violet, shifting his eyes around the place in curiosity. He kept following her until she led him until what he assumed was her bedroom.

As weird as he found this, he was even more shocked when he found Daisy and Lily sitting on the bed. There was something off about the atmosphere of the room. He felt as if the girls all knew something, and they were refusing to tell him yet. He did not let it phase him externally though; he put on his cool face like he did in any situation.

“So… what do you need my help with?” He asked

“Well,” Daisy started, standing up, “Every woman has her… needs.”

“Mhmm.” Gary said, nodding happily.

“We’ve heard that you are pretty good at satisfying those needs.” Lily stepped in.

“You have, now?” He asked, his voice full of swagger.

“You interested?” Violet finally asked.

“Beyond interested.” He said.

And with that, the conversation was ended. There was a brief awkward moment as everyone knew that it was supposed to start now, but no one wanted to start it. The moment did not last long, and suddenly, everybody moved at once. The girls swarmed to Gary; Lily was able to get to him first. His clothes flew off him before he could do much of anything. Daisy and Violet undressed themselves as well, while Lily simply dropped to her knees.

She opened her mouth and swallowed his suddenly exposed cock. She salivated over his somewhat erect member, making it nice and wet. Her wet mouth was able to do the trick; his dick sprung into full length. She briefly took her mouth away to flip her pink hair back and gaze at his size. The three girls all looked at it, hoping that he would on par with their expectations. They were happy to see that he was; his cock rivaled Ash in size.

Lily covered his rod with her mouth again, leaving Daisy and Violet out of action. Daisy improvised, getting down on the ground next to Lily. She went underneath her, and she took Gary’s balls into her mouth while Lily focused on his shaft. Violet got behind her sisters, sticking her tongue in Lily’s opening, while using one of her hands to rub Daisy’s.

Gary, Lily, and Daisy all moaned in pleasure at the same time; Gary was the only one clearly heard since he was the only one of them with nothing in his mouth. Lily and Daisy worked great in tandem, making Gary wonder if this was a first time thing for them. The combined joy that each of them gave him with their warm, moist tongues made him close his eyes.

He opened them back up though, for it was a lovely sight to see. Lily pushed her head all the way forward, swallowing his entire dick. To prove what a pro she was, she kept her head steady there. She flicked her eyes up, looking innocently at Gary as she deep-throated him. She kept her eyes on him as she pulled back on him inch by inch. When she finally reached the end, she pumped her hand up and down his member a handful of times before she stuck it back in her mouth.

Meanwhile, Daisy delicately flicked her tongue against his grapes. She teased around with him, lightly sucking and licking on parts of his sack. She tried to focus on the work of her mouth, but it was rather difficult to ignore Violet rubbing her crotch. Violet inserted a finger, sending it in circles to play with her. Daisy bit her lip to stay under control, and then she took Gary’s entire sack into her mouth to keep from moaning too loudly.

Violet continued to finger Daisy while also eating out Lily. She was messing with both of them, but they both did a pretty good job of not letting it affect the job they were trying to do. Lily was still able to bob her head up and down his long dick despite the bucking her body made in reaction to Violet’s tongue. Between the fact that it was getting hard for her, and because she did not want to Gary to cum, she stopped with her blowjob.

“Now it’s my turn.” Violet demanded, knowing what was coming next.

She laid down on her back on the bed, and Gary crawled on after her. He got on his knees, throwing her legs over his shoulders. He pushed into her slowly, watching her face light up in joy. He kept watching her, so he could know when to stop, but she seemed able to take him alright. Her face cringed up a little as he stuck in his last few inches, but she would be able to get acclimated to him.

He made nine shallow thrusts before giving her a long, deep push on the tenth. He repeated the same thing as he looked into Violet’s beautiful, almost maroon, eyes. Gary couldn’t lie, he had a little bit of a weak spot for eyes. In fact, her whole face was incredible to gaze upon. Her skin was smooth, showed little to no sign of make-up, and was a nice white tone. Her blue hair was not even strange to him; it just brought out the rest of her features with the bold contrast.

Daisy and Lily decided that they were done simply watching, and they got onto the bed too. Lily wanted some more of the action that Violet had given her earlier, so she crawled onto her face. Violet knew exactly what she wanted, so she inserted her tongue into her pussy once more. Daisy got in front of her, and she shoved her crotch into Lily’s face, forming an uncompleted Daisy chain (no pun intended).

Violet continued to take Gary’s cock while she attempted to give cunnilingus to Lily. She swirled her tongue around at the same time that Lily swirled her tongue around inside of Daisy’s vagina. Gary had taken his nine shallow pushes plus one long down to four short thrusts before one deep one. He could sense that Violet’s were walls expanding to help accommodate his presence.

The sound of mixed, high-pitched moans from the girls filled the room. Misty and Ash had gone away for the weekend, so they had the house to themselves, and there was no need to worry about the noise they were making. Gary listened to them; it was music to his ears. Trumping the noise was the sight. For all of the girls that he had been with, they just may have been the best looking.

Daisy had golden hair that went well with her bright green eyes. Lily was the only person Gary knew that could pull off pink hair. It was so attention grabbing that he hardly noticed her faded blue eyes. Violet, as already described, was very beautiful as well. All of them were fairly identical in size and fitness, and they all opted for their natural, pale, skin tone rather than a fake tan like a lot of girls.

Gary gradually used less and less of the softer, shallower pushes until they entirely disappeared. He went easy in terms of power, but he penetrated deep with his thrusts. Violet had stopped working her mouth on Lily to let out a loud shrill. This shrill was caused by the orgasm that Gary had managed to get out of her. She sighed happily as she got exactly what she had hoped for from him.

Gary let her legs down, and Violet rolled out of the way. Daisy jumped at the opportunity to be next, claiming Gary for herself. She pushed Gary onto his back and straddled onto him cowgirl style. She lowered herself down on his cock, gasping happily the whole time. Violet was content to take a nap, but Lily wanted to stay involved. She moved over to Gary, and she sat on his face.

He was disappointed to lose the view that he had of Daisy, but he was also more than happy to go to work on her. He rested his lower body, letting Daisy simply ride him at whatever pace she liked, while he licked around Lily’s pussy. He started with her outer labia, but ended up moving onto the inner labia, which was much more stimulating for her.

Daisy grinded her hips as she rode up and down at a moderate pace. She was happy to see that the rumor was true; he had enough size to please any woman. As far as her memory could tell, he was every bit as large as Ash was, maybe even more so. He was as tight a fit as she could remember ever having. She moaned quietly each time that she slid back down him.

She saw Gary use his tongue to attack Lily’s sensitive clitoris, which gave her an idea. Both of her hands were free, so she stuck one down and rubbed against her clitoris, never ceasing to slide up and down on Gary’s shaft. It added a whole other dimension of pleasure when she used her fingers along the most sensitive part of the human body. She started to moan even louder.

“Yes! Yes! Oh yes!” She cried out.

Right then, she was overshadowing Lily’s voice, but she was also voicing her own pleasure. Gary obviously had experience in this field, because he was pushing a lot of the right buttons. Heck, he was pushing a few new buttons. His tongue was soft, delicate and skilled. The feather light touch gave her a type of pleasure that was different from anything else.

Daisy had moved on from her grinding, and she was now bouncing on his dick. She had been in this position quite a few times in the past, and she was capable of flinging herself up and down at a quick pace. She knew how to control her curvy hips; she could make them move a lot when she wanted them too. Her fingers started to move more furiously as well, and seconds later, she finished with a cry herself.

“FUCK!” She screamed.

Being her greedy little self, she wanted to stick around for another turn, but she got off of so Lily could have her fun. She curled up next to Violet, preparing for a nap herself. Between the physical exercise, and the orgasm, sex does a great job of putting people to sleep. With Daisy and Violet off to the side, it left just Gary and Lily.

Gary took her arms and pulled her out of the bed. He bent her over the mattress, putting them in a standing doggy style. He pushed in about half of his length, but she asked him for all of it. Once he was given the green light, Gary just smiled and stepped on the gas. He pushed in his entire member, groaning as the third tight pussy of the day clamped down hard on him.

Once he managed to fit himself in, he wiggled around a little, double-checking to make sure he had enough room. Seeing that he did, he pulled out, preparing himself. The next time he entered, he pushed in one smooth motion. He pulled out quickly, only to reinsert himself, of course. He got a little bit faster with each passing minute.

He then started to put some major power into each thrust he made. He had incredible stamina, lasting two round and still having plenty left to give Lily a wild ride. He slammed his big dick into her, making her yell in bliss. She had never done a male dominant position with a man of Gary’s size before. She loved being the one in a submissive position.

“Oh! Oh, fuck me! Fuck me hard!” She let out.

Gary grabbed onto her hips now to give him more leverage. It was a good thing that Gary bent her over the bed, because otherwise, she would have fallen over for sure. Her body was forced into intense rocking movements each time that Gary pumped into her. He hit places inside of her that were very rarely, if ever, touched, with a lot of force.

Gary continued with the same style like a machine. He was one of those people that seems to never get tired. He just pushed into her powerfully over and over. He felt Lily have an orgasm but that did not stop him. She was the last one left, so she had to stick with him until he reached the end, which was ultimately closer than he would like. He did, after all, already go through two women.

In a well-rehearsed move of his, Gary entered rapid fire mode. Once he knew that he was down to his last minute, he gave his last-ditch effort. His penis was a blur as it shot in and out of Lily’s snatch. She began to howl like a mad woman as she was given cock like she never had been before. She woke up her sisters that had managed to fall asleep with all her noise.

“OHHH! AHHH! AHH! YES!! AHH!” She screeched

Gary put his smirk back on his face as he heard her scream. It was something that he had sort of become accustomed to. He continued to blast her with everything that he had until he felt that he was too close to the edge to risk it. He pulled out of her suddenly, flipping her around. Just as she started to look at him, a stream of cum exited his dick and was sent in a bee-line for her face. It came out in three long spurts, each one managing to land on her pretty face.

Gary flopped onto the bed exhausted. He wanted to take the nap that he had had delayed for this. The girls all scooted up next, curling around him to take a nap as well. Before she drifted off to sleep, Lily had one final thought about Gary. _Damn_ , she thought, _he really proved that rumor to be true._


	23. Winsome

**Summary for the Chapter:**

> Ash's needs a confidence boost after his bad loss to Anabel.

“Hyper beam!” Anabel shouted to her Metagross.

The huge white beam of energy struck Pikachu head on, knocking him straight down. Ash was stunned when Pikachu was unable to rise from the ground. His little buddy was down and out, and he had now lost the match to Anabel. He had been flat-out overpowered by her Metagross, which was something that he did not think was possible. It had even taken him three tries before he could finally defeat her powerful Alakazam.

He heard voices in the background that could have belonged to Anabel or May, offering consolation, but he did not listen to any of the words. He had been humbled, maybe even humiliated, in a match that he had fully expected to win. A handful of regrets coursed through his head once the disbelief had finished settling in his head.

He trudged back to the Pokémon Center to drop off his injured Pokémon and to go back to his room. Brock knew better than to bother Ash this soon after a bad defeat. He figured he would cool down and become approachable after a day or two. Because of this he took May and Max with him to do some sight-seeing while Ash did some thinking.

Just like he had after suffering bad losses, most notably to Richie in his first ever league championship, Ash contemplated on his training abilities. Should he even be a trainer? Would he ever reach the level that he always dreamed of? Was he wasting his time? The thoughts were obviously ridiculous notions to consider after one measly loss, but that was how Ash worked. He was rash, and he overreacted to things that were not such a big deal.

The joy that accompanied the winning streak that he was on before his battle with Anabel had disappeared in a flash. The rest of the day passed by with Ash hardly noticing it. He picked up his Pokémon after Nurse Joy took care of them, and he turned in early for the night. Pikachu was pretty depressed himself, so he just curled up next to Ash without a sound.

XXX

Ash arose early the next morning; his mood was only slightly better. Something compelled him to take a walk alone, so he did just that. He threw on his outfit and exited the building before any of his friends had woken up. He strolled about thoughtlessly, letting his subconscious direct his path of travel. After several minutes his feet parked him in front of the Battle Tower.

He took a second to comprehend where he had gone, and then he entered the tower. The building appeared to be fairly empty when he first stepped inside. He walked to the battlefield that was the setting for the cause of his depression. Not surprisingly, Anabel was present. She noticed him from across the room, giving him a sympathetic look. She knew how hard he had taken the defeat.

Ash was unsure as to why he had shown up in the first place. He had not been thinking about what he was doing until just then, and now he was questioning his motifs. He had not brought any of his Pokémon, so he could not attempt a rematch just yet. It wasn’t a battle that he wanted, but what was it? Did he just need to visit the scene of the past day?

Anabel started walking his way since Ash had frozen at the entrance to the battlefield. He did not retreat or advance forward; he simply waited for her to reach him. When she did, she placed her hand gently against his shoulder, trying to provide any comfort that she could to him. She waited for him to speak first, but she soon found out that that was not going to happen.

“You can’t be so down on yourself, Ash,” She consoled him, “You’re a great trainer.”

He mumbled something inaudible, but it sounded like he said something in disagreement.

“Honestly, Ash, you have to be extremely talented to get as far as you have. You’re a great trainer, and a really great guy too.”

Ash looked at her a little funny with what she added at the end. Even he knew that she was borderline flirting with him, and he did not know how to feel about that. He found her to be strangely attractive, yet it was only yesterday that he thought she was a boy. He tried to shove the thoughts to the back of his mind; he was probably interpreting her words wrong.

“I mean it.” She added with a small blush.

Now Ash was pretty sure that she was just complimenting him. He felt rather awkward about the whole situation. He was unsure about how to respond, or if he needed to respond. He still had not uttered a decipherable word in the conversation anyway. He thought she was a little cute, but again, he did not know how to say it or if to say it.

“I can sense how you are feeling.” She reminded him.

Now it was Ash’s turn to blush. He forgot how powerful her brain was in the art of empathy. Could she hear all of his thoughts? No, that would just be too freaky. He supposed that she could just get the overall feeling that was emitting from him. Heck, she probably understood how he was feeling better than he did.

“You’re cute.” She said with a smile, almost laughing.

Ash looked down, brushing his black hair away from his face. For some reason he felt that I he avoided her look that maybe the awkwardness would end for him. But then, he thought, did he want it to end. The more he thought about it, the more attractive Anabel appeared to him. Her lilac hair was so fascinating to him, as was the rest of her, personality included.

“So are you.” He finally spoke.

Anabel blushed like a schoolgirl. She already knew how he felt, but it was different when we spoke it out of his own mouth. She smiled as well as she ever had and looked at Ash’s face. He had lifted it to look at her, and they simply gazed at each other’s, both in the mouth and eyes. After a few seconds of looking at each other, something happened and the mood changed a little.

They both felt it, but Anabel was the only one who really understood it. She leaned in her head as slowly and inconspicuously as she could. Making a scene of it could very well scare Ash off in her mind. Ash only realized that the distance between their faces had decreased when she was practically right in front of him.

In somewhat of a shocker, Ash closed the rest of the distance at the same moment that Anabel jerked forward. Their eyes closed and their lips crashed together. Ash was taken aback a little by the feeling of her lips. They were much softer than he was anticipating, and they had a hint of a fruity sweetness to them that he was not expecting either.

They pulled back after a few seconds, breathing a little harder than unusual but nothing very noticeable. There was doubt and confusion in the couple eyes. They did not where they were supposed to go after that. Ash figured there was about only one place that you could go, so took one of his signature risks, leaning his head in for another kiss.

She took his lips happily, meshing his with hers. They leaned in more this time, making the kiss much more powerful than the one they started with. Seconds past, but neither one of them even thought about pulling away. Instead, they tilted their heads in opposite directions so they could deepen the kiss even more. Their heads started to move a lot more as the kiss became increasingly more electric.

Pulling away for air, Anabel spoke, “There’s a bed back there if you want to move there.”

It was a very daring move on her part; one that Ash might not have ever seen coming. His initial hesitation provided a seemingly endless moment of regret and terror for Anabel. The question had thrown caught him so off guard that it required a moment of thought, even from Ash. The heat of the moment shortened his thinking time, however.

“Yeah, of course.” He responded rather calmly.

Anabel took his hand and led him back to her room. She had her own room since she often just stayed the night in the tower anyway. She rented a home in the area, but she spent very little time there. The walls were purple, but they were a darker shade then that of her hair, eyes, and outfit. It was a small room, nothing much more than the bed.

Standing next to the made bed, Anabel leaned in to kiss Ash again. She opened up her mouth and unleashed her tongue this time, begetting Ash to do the same on his end. Her hands roamed down to his pants, where she was thankful that there was no belt to mess with. It took her a few attempts, but she managed to unbutton and then unzip his pants while still making out with him.

She pulled them down as far as she could without bending over before she moved on to his shirt. She undid the buttons with much more ease this time, and lifted the shirt over his head. It made them take a break from kissing, but it was probably for the best, since they were both having a little trouble keeping their lungs full of oxygen.

She stopped moving her hands now that she had him down to his boxers. Ash assumed it was his turn now, so he followed the order that Anabel had taken. He pants came off without much work at all, but her shirt was a little bit of a tougher challenge. He had a handful of buttons to take care of, and then he had to lift it over her body.

They parted lips for good once they were both stripped down to their underwear. Anabel saved Ash an opportunity to embarrass himself by unclipping her own bra, dropping it on the ground once she finished. She also went ahead and took the honors of removing her final piece of clothing, slipping it down her legs. She was uncomfortable being nude in front of Ash, but she tried not to let it show.

Ash knew that he had to follow up by getting rid of his underwear too, but he was nervous himself. His penis was already letting itself show in its attempt to poke through the fabric, but there was still something unnerving about actually putting it out in her field of vision. He knew he had to do it though, so he dropped his green boxers to the floor.

They took in each other’s body; each of them thinking about how attractive the other was. Following a few seconds of checking each other out, they moved on to the even they had been building up for. Ash took Anabel in his arms, laying her on the bed, while he crawled on top of her. He looked down at her, waiting to see if there were any last minute doubts.

She said nothing, and Ash could only see excitement in her eyes, so he pushed himself in gradually. He was waiting for her hymen to stop him, but it became apparent that no such thing would happen. Being a virgin himself, he found it to be disappointing that she was not one as well, but he tried not to let it show.

He guessed that she had only been with a man a few times because she was as tight as he could have imagined. He pushed in a little over half his length, amazed at how much pleasure it was bringing him. The place that had only ever caused him pain, via being hit or punched there, was now making up for all of that with an intense joy.

He had completely forgotten about the match from the day before and how down he was feeling about himself and his career. The heat that came from her body and combined with his seemed to form a relaxing steam that temporarily relived any issues he was having. Anabel, despite not having any major issues at the time, felt the same way.

His cock fit inside of her so well. It was not such a monster that it caused pain, yet it was also not so small that it would not satisfy her. She laid down against the bed, using next to energy while Ash penetrated her. She trusted him to make her feel good, and it was working well. He was moving slowly, just the way that she liked it.

“Ohh!” She moaned constantly.

Ash figured that since she seemed to be happy, that he must be doing something right, so he did not change anything. He was using full thrusts, maximizing his time inside her, while also staying out just long enough for her to get a little antsy waiting for him to plunge back in. He had worked into a very nice rhythm, perfecting the time and speed of his thrusting.

Anabel would never have known that he was a virgin if she had not managed to sense it with her incredible mind. He was performing impeccably for his first time. She felt him start to divulge his full member into her as a few minutes passed by. It was no trouble for her to fit him, and he also was getting deeper into her pussy.

“Oh, Ash!” She moaned louder.

Ash started to feel more and more proud of himself as he listened to Anabel praise his work. His confidence, and/or maybe his lack of experience, got the better of him in the end though. He began to lose the rhythm that he had, going a little bit faster and a little less controlled. He felt something building up inside him, and the closer he got to his climax, the more he wanted to reach it.

He pushed in one final time, losing his cum with a yell. Anabel was shocked at how fast that had turned around, but she gave a little yell too, faking her orgasm. It honestly was not a very convincing lie but Ash fell for it. His eyes suddenly shot open seconds after he had climaxed inside of her. It took him a few moments to get out words.

“I just- oh- oh my god- I-I-I um… finished inside you. A-a-and I didn’t use a condom or anything.” He stumbled out, sweating.

Anabel just giggled at him.

“Oh I take a pill for that, don’t worry.”

Ash sighed in relief; he really thought that he had messed up there. He had been terrified.

“You’re so cute.” She told him, giggling at his goofiness.


	24. Xenos

**Summary for the Chapter:**

> Ash remembers Domino, but her memory of him has been wiped, so Ash exploits his advantage.

**Notes for the Chapter:**

> Xenos, the theme word, refers to a stranger.

The sun was setting on Ash’s first day of traveling alone since his very first day. He loved his friends dearly, but he felt that he needed to travel alone if he wanted to be serious about reaching his goal of Pokémon Master. He figured there was no better place to start than his roots, so he set off for another journey through Kanto. Nostalgia swept through him as he walked along the dirt path.

Every tree he saw was another memory appearing in his mind. He remembered the conversations, fights, laughs, and mishaps that happened in the past fondly. He tried to keep his mind form drifting, he would have plenty of thinking time at night, for he needed to find a place to set up camp. However, he was not in an ideal location.

He had cleared the forest that he was walking through, and he had entered a highly mountainous terrain. He did not want to turn around, so he pulled out his sleeping bag at the foot of the mountain. He let out his Pokémon to get some exercise, while he went to look for some firewood. He was going to attempt to cook himself dinner, and who knows how disastrous that could have gone.

In a short time he was able to get a big bundle of kindling, so he lit a match and started his fire. Brock had always held him responsible for getting the fire started, and keeping it going for a little, so this was fairly easy for him. As he waited for the fire to get going, he pulled some of Brock’s famous Pokémon food out of his bag for his hungry partners.

Unbeknownst to him, he was being watched. A woman, perched on a ridge of the mountain, observed him keenly. She was not as interested in him as she was his Pokémon. He seemed to have some powerful and rare ones, including a giant Charizard and a shiny Noctowl. She smiled, thinking of what a great addition they would be for the Team Rocket cause.

She waited for the traveler to leave camp once more patiently, breaking her cover once he was out of sight. She scampered down the tough mountain path; she was in a race against the clock, and she did not even know how much time she had. Her agile maneuvers allowed her to reach ground level in a matter of seconds, without anything more than a scratch on her body.

She pulled out her signature “tulip”, pointing it in the direction of Charizard. Before she could use it, she heard a rustling of bushes, and Ash reappeared. There was something strange about it him; it was like she had seen him somewhere before. She trained in vain to give him a name, or to find out how in the world she would have known this young man.

She tucked her weapon away, forgetting about her goal in the first place. The man was so intriguing to her. She became so caught up in staring at him that she forgot that she was not expertly hidden. When Ash happened to look over her way, he saw her clearly. Mentally slapping herself, the woman tried to think of what she should do.

There was no doubt that he saw her; they even locked eyes. Sighing, the girl walked in the direction of the person who spotted her. She dragged her feet, taking as much time as she could. When she finally reached the fire, she stopped and looked at him. They were both waiting for the other to say the first word. Ash, being as impatient as he is, caved in first.

“Who are you…, 009?” He asked, reading the number off her uniform.

“I go by Domino.” She told him for some reason.

She had acted off pure instinct, so she gave him her actual name. Being an important Team Rocket officer, that was pretty stupid of her. In fact, when she said it, the man in front of her had a change of demeanor. The name obviously meant something to him, proving that the two of them had been acquainted somehow in the past. Hopefully he would inform her.

“Where do I know you from?” She questioned him.

Ash shrugged his shoulders, giving her a face that implied that he did not know the answer.

“Don’t play games with me.” She instructed.

Ash had given his best try at acting it off as nothing, but he was no actor. He recalled Domino quite well from the incident at Mt. Quena. He also knew that she had no memories of what happened, yet he did. He could not tell her who he really was, or she might be able to remember what had happened, and she might attempt some sort of revenge. He needed a convincing lie, but he was busy taking in how good she looked.

“Alright…” He began, throwing his arms up in surrender.

“We- uh- had a one-night stand, don’t you remember?” He asked, wondering why the hell that was his lie.

“No, I don’t remember that at all.” She said, skeptically.

“Of course you don’t. You had your memory wiped.” At least that part was truthful.

“My memory was wiped?” She said with a snort. She thought he was full of shit.

“By Mewtwo.” He said.

Her eyes bugged when he said that. She was not confident about the reasons as to why, but she believed his last sentence. She could not remember the day or days that he was referring to, but a big handful of the pieces to the puzzle arranged themselves when she heard those words. Those two simple words had forced her to trust everything he said. She hadn’t said anything, but Ash could tell that he had pulled it off.

“Maybe,” he said, returning all of his Pokémon, even Pikachu, “I could jog your memory?”

Why Domino considered the proposition was beyond her. Granted, he was cute, and apparently she had slept with him before, but that was no reason to do it again. The main reason was because she did want to have her memory jogged. She wanted to remember the things that been wiped away from her memory. She knew something important must have happened in that time period.

“Maybe you could.” She said after he stepped towards her.

Ash was fairly surprised at her response, but he did not let it show. He attempted to put a smirk on his face, just like Gary. He leaned in closer while Domino stood her ground. She had no real desire to lean in herself, but she had decided not to stop him. She kept awaiting the moment when his lips brushed against hers, but it was taking forever.

Eventually, he met her red lips so softly that she might not have even detected it had she not been expecting it. The feeling became more noticeable with each passing moment; Ash continued to inch closer to her, pressing harder against her lips. Something strange happened to Domino when she felt his lips. She reacted naturally. Not naturally as a Team Rocket agent, but as a person. She kissed him back.

Her initial reason for showing up, to steal Ash’s Pokémon, had long since slipped her mind. There was something so intriguing about this man, whose name she still had not learned, that it diverted her attention completely. There was the mystery of what circumstances they met, and there was the simple fact that he was a charming man.

She pressed back against his lips with the same intensity that he gave to her. It was full reciprocation on her part. She felt him wrap his arms around her, moving his sides along her body. He rubbed her sides at first, and then played with the flaps of her uniform. Ash found the belt wrapped around her waist, and worked it off, now being able to understand why women sometimes struggled to remove his belt.

He pulled away from her, taking off her black uniform off in the process. This left her in a white, striped skirt, which he got rid of as well. Ash growled hungrily when it was revealed that she had no bra on. She responded by getting him topless as well, removing his vest and t-shirt. Ash leaned in and kissed her again before she could get too carried away in undressing him.

He hugged her tightly, causing her boobs to press into his chest. The soft, round pillows felt fantastic when they came into contact with him. It excited him even further, which led to him opening up his lips. Domino followed suit, and once she did, their tongues clashed together. They made out while their hands traveled down to get rid of any remaining clothing.

Ash found her underwear and was able to pull it off of her quickly. Domino had to give a little more effort, but she got his jeans off soon enough. Before she could try to pull his boxers down, Ash brought his tongue back into his own mouth. Domino did not know what he planned to do, nor did she care. She took charge, dropping down onto her knees and yanking his underwear off.

She stroked his member once it was revealed. She was pleasantly surprised at the size of him. After petting him with her fingers, she stuffed him in her mouth. It had been so many ages since she had been with a man that she forgot what cock tasted like. There was no food that she could compare it to, but it was still pleasant to suck on in her opinion.

And it was certainly pleasant to be the one getting sucked off. Ash was stunned at her eagerness to go down on him; most women needed to be told or asked, but not her. She placed a soft hand on the back half of his cock, slowly rubbing it while she sucked on the other half. She would use her tongue to lick him at the same time that she would stroke him with her hand.

Ash groaned while Domino polished his knob. Her wet mouth moistened his cock as well as massaged it. She briefly retracted her head from his phallus, placing it down on his balls. She stroked his rod a few times with both of her hands while licking his nuts. She did not stay down there long enough to make a show, returning her mouth to its original location in a matter of seconds.

This time she removed her hand, moving her head further down. She did not attempt fit all of him in, but she was able to cover most of him. She bobbed her head steadily, keeping control easily. Her tongue had a mind of its own; it could operate without her even thinking about it. It swirled and licked every available inch of meat that it could.

Ash continued to praise her on her work. She performed like a veteran even though she was probably closer to the inexperienced side. She continued to host his cock in her mouth until she felt his cock bulging. Sensing that he was almost ready to blow, she immediately stopped all of her actions and pulled her head off of him.

“You’re going to pay for that.” Ash told her as she smiled cutely.

He pushed her from her knees to the ground before he picked up her legs. He pulled on them until her torso was at the level of his. The position required for Domino to do a handstand, something that Ash knew she was capable of. Ash slid his dick into her while she was still slightly caught off guard. She cooed as he entered her.

“Oh God; you’re so big!”

Ash could have taken this as a sign to start out slow, but he was not in this to be nice to Domino. For one, he knew who she actually was and the terrible deeds that she has both attempted and completed. Not only that, but she had left him hanging from the blowjob just before. He did not want to cause her any serious pain; he wasn’t that kind of guy, but he was not afraid to give her a little.

Because of that, Ash kept pushing in until his full length was stuffed in her tight hole. Domino gasped and grunted; she was obviously struggling to fit him. Ash slowly pulled himself out, and then pushed all the way in. Her pussy clamped down on him so hard that it almost seemed like it should hurt. Of course, it did the exact opposite, giving him intense pleasure.

He could not have gone quickly if he wanted to because of how much his cock was getting squeezed. It was a good thing for Domino that that was so, for she was having a hard enough time. Even though she had the smoothness and flexibility of an Olympic athlete, it was still hard to do a handstand while also taking in a dick that really did not fit.

Ash tried to pick up the intensity now that the two of them had had a few minutes to adjust. The time between his thrusts went down, while the force behind them went up. Domino’s body started to shake because of it, despite her full efforts to stay balance. Ash appeared not to notice; he simply began to push into her harder.

Eventually, it was too much for Domino to handle, and she fell over. Her arms collapsed from underneath her, dropping her entire body down to the ground. Ash did not let it phase him though. He laid down right behind her, opened up her legs to give him an access point, and reinserted his penis. Domino, again, was experiencing some pain.

Falling down did not really hurt too badly; it isn’t like she fell from far or anything. It was just the working out that Ash was giving her inner vaginal walls. He was stretching them further than they ever had been before. Each time that she thought she was getting used to it, Ash would take notice and notch it up another level. He had worked up to a medium pace, using jagged thrusts.

“Oh, Oh, OH!” Domino grunted out.

She felt herself have a small orgasm that she could not have held back even if she tried. Ash’s cock was just a machine; there was no slowing down. She was not doing much of any exercise, yet she needed a break. That break did not appear to be coming anytime soon though. Ash just kept thrusting in, increasing at a steadily increasing pace.

Ash, on the other hand, was having one of the nights of his life. He had managed to trick one of his attractive enemies into bed with him, and she was giving his cock possibly the greatest ride of his life. He enjoyed the sounds of her pushing her body to the limit; it helped motivate him a little further. It was one of the reasons that he was managing to last longer than he normally did.

‘AHH!” Domino shrieked.

Ash had finally worked up to a fast pace. He was only holding back a little now. Domino found that the louder she yelled, the more it helped with her pain. Ever since he had penetrated her, it had been a mixture of pain and pleasure, but the pleasure was starting to take center stage. In some odd way, the pain helped contribute to the pleasure.

Ash felt his clock ticking now that he had finally worked up his current pace. Sensing this, he threw in the last bit that he had been holding back. He shoved his full length into her, repeating the motion a countless number of time. He focused all of his energy into his pelvis, thrusting in and out as quickly as possible. Right before he finished, he was wise enough to pull out and excrete his cum onto her butt.

“OH FUCK!” Domino had one last powerful orgasm almost simultaneously with Ash.

After a few minutes of laying and panting, Domino finally asked the question she hoped would clear more things up.

“What is your name?” She asked.

“Just a second.” He mumbled back.

A confused Domino watched him pull his clothes back on before walking away to his tent. She put her own clothes back on as she awaited his return. She got a little worried as two minutes passed by, but then the man reemerged. He held a folded piece of paper in his hand as he walked up next to her once more.

“This will explain everything. Just wait a night to open it, please.” He told her.

“Oh… alright.” She conceded.

“Goodbye then.” She waved, without garnering a farewell from Ash.

She did not know why, but she felt that she owed it to that man to not read the letter in front of him. She was not going to wait until tomorrow, but she figured she could get out of sight before tearing it open. She scaled her way back up the mountain, reaching the Team Rocket base. She flashed her ID to get in, and then walked to her office. Turning on the light, she read:

I made up that whole story. I have no idea who you are.

Down below, Ash had packed his tent back up, running away in the night with a huge smile on his face.


	25. Yoga

**Summary for the Chapter:**

> Yoga class leads to some action for Ash.

“Now close your eyes.” The teacher instructed her class.

Ash struggled to hold the position that the class was supposed to be in. He kept his eyes open because, well, that was the reason he was in the class in the first place. He awkwardly attempted all of the stretches from his spot in the back of the room, but that was not his primary concern. He spent the entire class time checking out all of the females.

His friends all teased him, calling him gay, for enrolling his name in a “girly” class. He shook off the abuse, for they had it completely wrong. He was in the class to scope out the girls, and hopefully, get laid. There were a fair share of girls who he wish did not wear the tight pants required for yoga, but those same pants really showed off the hot girls.

So as everyone else closed their eyes, Ash honed his in on a particular hottie. She had short, but vibrant, red hair, and a trim body. Her body was stretched forward, raising her ass in the air. She was directly in front of Ash, and he drooled at the sight of it. It was begging to be felt, but he had to control himself. For now, at least.

He had found his target girl for after class. Another 15 minutes passed before the teacher dismissed the class, telling them that the session had ended. Ash waited for the girl to exit so he could follow her. She happened to catch his eye in the process; she gave him a quick look down and smiled. Ash grinned back, but she had already left the room.

He scampered off in the direction she headed. Despite having plenty of time to think through a plan, he had not done so. He wasn’t sure if he should follow her for a little, or if he should just tap her on the shoulder right now. Stalking her would be way too creepy, but the gym was too crowded to make a move. He ended up deciding to attempt conversation.

“I’m Ash.” He said, running up next to her.

“I’m Georgia.” She told him, slightly curious as to why he wanted to talk.

“You been going to this class for a while?”

“A few months. Well, I walked here, so I’ll see you next class.”

Georgia headed to a walking path, leaving Ash behind. Ash clicked his teeth together while he brainstormed. Running after her would require a pretty solid excuse, and/or would come off as desperate. That thought made him hesitate. He had to make a choice quickly, so he decided that he WAS desperate, so what the hell.

“I could go for a walk.”

It was hardly an excuse, but she reacted well. She gave him a smile, alleviating his fear that she would tell him to leave her alone. She might have if it had been someone else, but there was something about him she liked. He was cute, both in personality and appearance. She liked how willing he was to chase after her. It wasn’t desperation in her book as much as it was giving an effort.

They talked for a few minutes, getting to know each other a little better. Ash had turned the conversation to Georgia’s personal life, and she revealed that she was single through a quick anecdote. The fact that she brought it up made it a lot easier for Ash since it let him avoid asking her. Now that a brief silence had fallen he could move on to a different question.

“Well, Georgia,” He started, unsure, “You’re a very fascinating woman. Could I ask for your phone number?”

“You could.” She said slyly.

Shaking his head and chuckling lightly at her response, he asked her correctly, “Would you give me your phone number?”

“Don’t you think that’s a little forward?” She asked, halting from her walk.

“No. This would be a little forward.” He told her after stopping right in front of her.

He had no idea what gave him the confidence to do it, but he kissed her. It was a short peck, but a kiss nonetheless. His eyes widened a little when he finished because he even surprised himself. Georgia’s mouth hung slightly open and her eyebrows raised themselves. The only emotion that Ash could read from her was shock. He braced himself for an angry reaction, yet hoped for a more accepting one.

“You’re confident. That’s hot.”

Something between relief, joy, and a little bit of embarrassment flooded over Ash. Her words, “That’s hot,” suddenly made it a lot hotter. He had managed to pull off the kiss successfully, but he wasn’t sure how much more he should push it. Going in for another one would be another gamble, but then again, she had told him that his confidence was hot. 

While Ash scrambled to make yet another difficult decision, Georgia had made up her mind. She wrapped her arms around Ash and kissed him; however, this one actually lasted for a longer time. Ash reacted quickly by his standards, and he started to kiss her back. He brought his arms, wrapping them around her waist. Her arms remained around his neck, but his started to move.

His right hand found itself creeping downwards. It eventually found its target; the target it had been yearning to touch since watching her stretch. Her butt was not large, nor was it small. It fell somewhere in the middle, but the more important fact to Ash was that it was firm. She obviously attended the gym on a fairly regular basis, keeping her in great shape.

He squeezed her buns a couple times each, rubbing them in the process as well. His hand moved up just a little bit, finding her waistband. He started to tug on it, which brought a reaction from Georgia. She broke off the kiss and grabbed his adventurous hands with one of her own. Ash feared that he had taken it a step too far.

“Ash… we’re outside.” She informed him.

“Exciting, huh?” He said, placing his hand over her butt again.

Georgia lightly bit on her tongue, considering the proposition. She turned her head around to see how far away they were from any highly public areas. There were no people, or even buildings, visible. Having sex outside was on her bucket list, but it was just so unexpected. She was with a guy she had only met less than an hour ago, and she had hardly planned on this. Then again, the spontaneousness is part of what made it so special.

She said nothing, but in doing that, and with the twinkle in her eye, Ash knew that she was saying yes. He took his hands off her butt and went to work on her shirt. She had been wearing a pink tank top, but Ash removed it from her body with her assistance. He pulled her tan colored bra down to her stomach, revealing her boobs.

The training bra that she had been wearing had been slightly deceiving when it came to her breasts. They were a bit larger than he was expecting; they fell somewhere in a B cup range. The hand that he had been using to fondle her butt left its current position and found itself fondling her breasts. Not wanting to ignore her other boob, he brought his other hand up to massage it as well.

While Ash happily groped her chest, Georgia kept her head on a swivel. She may have consented to Ash’s wants, but that did not mean she wasn’t nervous. She felt Ash remove one of his hands and replace it with his mouth. His hand snaked its way back to her ass, rubbing it in circles once more. She had assumed they would go for a quickie, but evidently, that was not what Ash had in mind.

Heavy breaths trembled out of Georgia as Ash sucked on her breast like a baby. He sunk his teeth into her nipple as lightly as he possibly could, emitting a loud grunt from Georgia. She bit her lip immediately afterwards, feeling guilty for making a noise. She grinded her legs together in another attempt to keep her satisfied and quiet.

Only then did she notice how impatient her body was getting. She was getting wet in her lower regions, and Ash had sufficiently gotten her nipples hard. Ash had either not noticed or cared the whole time because he stopped nothing. His mouth had moved over to her left breast, and his hand was applying light smacks to her butt, but nothing else had changed.

“Ash...” She muttered softly.

Her verbalization showed to Ash that he was doing his job. She was antsy, but full of enjoyment at the same time. Her breasts were clearly very sensitive to her, so he focused his attention on them. He still felt up her butt through the thin fabric of her pants, but he concentrated on her knockers, driving her crazy.

His index finger and middle finger squeezed down her open titty. He followed about a squeeze with soft touches and rubs. He bounced back and forth between the two for his opening act, before eventually bringing in the rest of his hand to join in. She groaned as his whole hand was able to cover her whole breast.

Ash tried to be as sneaky as he possible could be, but it was hard to pull of his next deed undetected. His hand on her butt drifted up to her waistband again, but he was not stopped this time. He peeled off her yoga pants slowly, with care. He worked them down to her ankles and left them there. With his face mushed into her breast, he had to do everything blind.

His attention to her boobs went uninterrupted, but his free hand was on a different adventure. He crept it up her smooth legs, feeling the goose bumps that he was responsible for. After finding his way to her underwear, he was able to detect a pool of liquid practically covering the panties. This observation put him in even less of a hurry.

He rubbed his hand over her camel toe in a teasing fashion. He felt her bucking her hips in minor resistance. After he felt that he had worked her up sufficiently, he began to prod her through her underwear with his pointer finger. The cotton material restricted depth, but did no such that for reactions. Georgia’s core was a raging fire.

“Asshhh!” She held out his name, whining.

By this point Ash thought he had played with her boobs long enough. He tore his mouth from them, ready to give her attention somewhere new. Choosing to give her some relief, he pulled her underwear down to her ankles, joining them with her pants. He reinserted his index finger along with adding in his middle finger. He felt like he stuck them into a hot sauna, for her pussy was beyond wet, and her inflating temperature could have almost turned the liquid into a gas.

When he finally stuck his fingers all the way in, Georgia felt a small wave of relief. It wasn’t all of what she wanted, but it was one big step closer. Ash ended up adding a third finger, his ring finger, to the mix after a minute. He started to slide his fingers in and out at a fast pace, listening to Georgia’s breaths become sharper and quicker in the process.

He slowed down to a near halt randomly, earning a groan from Georgia. Just when she was starting to feel some satisfaction, Ash yanked it away like a quarter on a string. He was playing with her, just like he had been the whole time. Before he could start up another session of fingering her, Georgia decided that she had had enough.

“No more. Just give it to me.” She said, grabbing his hand and pushing it away.

Georgia began to tear away at all the clothing on Ash. His workout shirt was over his head before he could react, and his pants disappeared in the next instant. Left in his boxers, Georgia could see a big bulge emerging from him. She petted his clothed dick lightly with her hand, getting a feel for how big he was. She continued to stroke him until Ash was the one getting impatient.

It could hardly be considered revenge since she did not give him half the struggle that he gave to her. When she pulled his underwear off and his meat popped out, Georgia’s mouth opened into a shocked smile. He had felt big from when she was stroking him, but there was something different about seeing it out. It was up and ready to go.

Just when things were about to get started, Georgia felt something on her shoulder. She had a hypothesis of what it was, and when she looked up, her guess was assumption was confirmed. It was starting to drizzle. She looked at Ash unsurely, but he was having no second thoughts. He joined her on his knees, and then he moved her to where she laid on her back.

He separated her legs, throwing them on opposing sides of his abs, and positioned himself at her pussy. He pressed his tip against her entrance and circled around it a few times. He could feel the warmth from her insides emitting out and breathing on his cock. He brought it close enough to come in contact with her outer lips, but left it there.

“You sure you still want it?” He asked in a teasing manner.

“Ash, please!” She said desperately.

“Please, what?” He said smiling.

“Please fuck me.”

“You don’t sound like you want.” He told her, rubbing his cock in circles. He knew that he might be pushing it, but he felt like he could push her as far as he wanted.

“Fuck me, Ash.”

“You want me to fuck you?” He asked, playing one final game.

“YES!” She screamed.

Ash finally obliged, sticking his dick into her yearning pussy. With all of the buildup that he put into it, there was no way he could start slow. He shoved in his full package, putting plenty of power into. It was a little difficult to start off so quickly, but it was the path that he paved for himself. He accelerated the tempo faster than he had done with anyone.

For Georgia, it was what she had been waiting for, and then some. She had been so anxious that she set the bar pretty high for Ash, but he was delivering the goods. It wasn’t that Georgia had gone some ridiculously long time without sex, but Ash had managed to flip her switch. He’d gotten her as horny as she could ever recall.

The drizzle turned into more of light rain, but it was hardly noticed by either Ash or Georgia. They were too into it to notice what could be considered a nuisance. The only real difference it made was wetting their hair and body, but they had been a little sweaty beforehand anyway. Many girls dream of getting kissed in the rain, but it was not very common to make love in it.

Georgia looked around nervously, for she had a sudden remembrance that her and Ash were outside. There were still no people, so she felt safe to let out her contentment. She moaned happily as Ash filled up her hungry pussy. It had easily been years since she had gotten a fucking like the one that Ash was giving her.

Her breasts were shaking violently, but that rapid motion had nothing on the rapid motion from Ash. His shaft was speeding in and out of her entrance at a frenzied pace. Watching the two of them go at it the way they were; hard, rough sex, on the road, in the rain, one might have confused them extremely horny animals.

Ash looked to his side, thinking he heard something, but saw no one. The rain continued to pick up, grabbing the attention of both of them. Neither one cared enough to stop what they were doing though. Georgia leaned back, throwing her head back in the process, and cried an extended moan into the storm. Her eyes were closed for a couple of reasons, one being the rain, and the other being the man stooped in front of her.

Ash’s face was scrunched up; he was obviously digging down to find something more to give. He’d already given her the gift of two big orgasms, with a third on the way. Still, he wanted the closing moments to be something unforgettable for Georgia. Every time she was with a man, he wanted her to look back and think of the time with him, in the rain.

He was going to be the unreachable bar that everyone else would have to gaze up at. Nothing was going to top the pounding that he gave her out the in the now pouring rain. Panting heavily, Ash gave her one final, hard thrust when he finally exploded into orgasm. A crack of thunder sounded simultaneously with his finish.

He felt her reach her climax at the same time, but his overpowered hers. Since hers was a third, it did not carry the same power as his lone blast. Once he felt his stream of cum stop, he pulled out of her. Georgia was laying almost helplessly on the ground after the intense experience. Staying in her position sounded great, but the thunderstorm made that sound impossible.

“How about we head back to my place, and maybe I can show you what yoga lets your body do?” She proposed.

Ash wasn’t expecting a round two, but it was a thoughtless yes. The two of them dressed quickly, anxious to get going. They took off at a light run, considering they were quite a bit behind schedule.


	26. Zesty

**Summary for the Chapter:**

> Ash finally wins a league tournament, and some celebration is required.

The first emotion to overcome Ash after the biggest victory of his life was pure joy. After years of hard work and defeats, he had finally done it. He’d finally won his first league championship. He sprinted out onto the battlefield once the judge had ruled the match in his favor. He scooped up a physically exhausted Pikachu, hugging him and laughing his happy, childish laugh.

“We did it, buddy! We did it!” He kept repeating.

Those were the only words that he could even think of. Pikachu was too worn out to celebrate with Ash just yet. It’s often a cliché for competitors to “leave it all out on the field” or to “give 100%,” but Pikachu had literally done it. He fell asleep despite the ruckus created by the fans. Communication was next to impossible for anyone within the stadium that seemed close to causing an earthquake.

Without even noticing what he was doing, Ash shook the hand of his opponent. He walked off the field afterwards, but Ash stayed. He soaked in the moment as much as he could. It was all he had ever dreamed of and more. The thunderous applause, the feeling of accomplishment, and the sight of his friends and family that had come out to watch his match formed a trifecta of emotions.

A reporter approached Ash to interview him. He could not think of her name at the moment, but he recalled seeing her on TV when she interviewed the winners of big tournaments. Realizing that she was coming to talk to him suddenly made it all so surreal. He was now the one on TV, being watched by Pokémon-obsessed kids just like him when he was younger.

“What a match!” The reporter exclaimed, “How are you feeling?”

“It’s all so…wow…I mean, it just feels like a dream, you know? I’ve always imagined being in this position since I was a kid, but now that is has actually happened… wow.” He finished, shaking his head in disbelief.

Slightly surprised at his ability to answer a question, however simple it may have been, Ash’s emotions took a little bit of a turn. His joy was still there, but it was being overshadowed by disbelief and shock. A simpler way to express how he was feeling might have been to say that he was stunned. The magnitude of the moment had become apparent for Ash the more that he thought about it.

“Can you take us through the battle? What was your strategy?” The reporter asked him.

XXX

After forcing himself to focus on the questions, the rest of the interview and the rest of the day flew by for Ash. His Pokémon were taken care of by a Nurse Joy on site while he went back to center stage for the awards ceremony. He accepted his trophy, holding it in the air to show it off. The crowd exploded for him once more as he was officially declared the champion.

The only thing that brought Ash even a little bit down was that he could not share his platform with all his friends that had helped him get to the stage. His friends were a vital part of his success, and of course, he could not have gotten to this point without his Pokémon. They were the ones fighting the battles after all.

He was then escorted off the field by officials. After being led back into the behind the stage area, he was handed all sorts of papers that he hardly cared about. The main one that he needed to keep track of was his itinerary. He had banquets, meetings, conferences, etc. that he was required to attend now that he held an official title.

There were no real long term commitments, just things for the following week. He was given the rest of the night to recover and celebrate. He was told that his Pokémon needed more attention than they had gotten at the stadium, and had been transferred to the Pokémon Center to spend the night there. He was a little bummed that he could not see them until the next morning, but it was not too surprising considering the beating they had taken.

When he arrived at the hotel he was staying at, he was surprised by his friends and family. He knew that they were all staying in the same hotel so they could watch him throughout the tournament, but he hadn’t been expecting the gathering. Countless people approached him, telling him how proud and happy they were for him.

Most of the people who had come to watch him had booked trains/flights for the day of the final match, so they had scramble off. Only a handful of people were actually staying around for another day. Among them were some of his former traveling partners, such as Brock, Misty, Tracey, May, Max, and Dawn.

As much as he wanted to talk with all of them, he also wanted to rest. He told them that he was going to take a nap, and that he would try to get with them later at night. He took the elevator up the third floor, walked to room number 320, and slid in his room key. It took the poor kid three tries to actually get it the right way, but once he did, he went straight for the bed, falling asleep within a minute.

XXX

The rest of the crowd headed on back to their rooms as well. Misty, May, and Dawn were the only ones on the same floor as Ash, so they walked past his room on the way to theirs. Misty and May walked on by without paying attention, but Dawn noticed that Ash had not closed the door all the way. It was just barely cracked open.

She pushed it open and poked her head in, making sure that she that it was, indeed, Ash’s room. She saw him snoozing on the bed, so she backed out to leave him undisturbed. Before she closed the door back, she spotted his room key sitting on a table by the door. She took it with her, smiling as she closed the door behind her.

Her two roommates gave her a funny look when she ran back up to them. They’d watched what she had done, and they wanted an explanation. Dawn waited for the three of them to get inside their room before she told them what she was planning on doing. She debated in her head whether or not she should ask them, but in the end, she went for it.

They agreed.

XXX

Ash was still sleeping hard when a knock sounded from the door. He slept through the noise, and the person who knocked on the door unlocked it and walked in. She left the room card outside the door as she closed it behind her. Ash was still sound asleep, sprawled out across his bed. He had been too lazy to get underneath the covers. All he had done was thrown his hat, jacket, and belt off.

Working as silently as she could, the intruder crept over to his bedside. She tugged as lightly as she could on his long khaki pants. Miraculously, she managed to lower them by a couple feet without waking the sleeping man. She figured that repeating the process with his boxers would be a tough feat, so she opted for a different route.

She reached in through the hole in the front of his boxers with a finger so she could adjust his unaware member. She pulled it over so that it poked its way through the very same hole. After checking once more to make sure that he was still sleeping, she attacked. She brought her mouth down, taking in his cock with it.

This was enough to wake Ash up. He opened his eyes to the sight of Dawn dressed as a hotel maid, giving him a blowjob. She flicked her eyes up at him, but she kept his cock in her mouth. Ash stared bewilderedly into her dark blue eyes. She looked back at him seriously and intently, finally detaching her mouth so she could speak.

“Room service.” She told him, ripping his boxers off to give her full access.

She dropped her eyes back down onto the object she had in her mouth. Her hot, wet, mouth had worked his previously limp cock into a full-fledged boner. Ash was still stunned to a point of silence and paralysis. He had not said anything to stop her, nor had he moved to stop her. Once he had had time to think about it, and time to soak in the feelings she was causing, he realized he did not want it to stop.

He moaned out softly in pleasure, expressing to Dawn that he was going with it. Normally, waking up after a long nap feels absolutely dreadful, and quite often ruins the rest of the day, but that was not the case this time. In fact, it was the happiest he could ever recall being after waking up. Dawn was working magic with her mouth.

Ash craned his head to stare at the bluenette as she bobbed her head along his shaft. Her hair was straightened down just like always, reaching about the midway point of her back, and her outfit made her look downright sexy. She had on one inch black heels, along with black pantyhose that reached way up her leg, all the way to where her skirt left off.

Her black mini skirt did not cover much past the minimum. It cut off just below her thigh from the bottom, and also showed off a little bit of cleavage on the top. There were patterns of white around the stomach as well as the neck and shoulders. If it was not Dawn wearing the uniform, it would have fooled Ash into thinking that it was a real maid uniform. It was very realistic.

Ash leaned forward into a sitting position, slipping his shirt off. Watching Dawn go to work on him in her cute outfit got him antsy. He wasn’t intending to be rude or anything, but he simply had to cut her off short. He pushed her head away and hopped off the bed to join her. As much as he just wanted to tear her outfit off of her, Ash realized that it was probably pretty expensive and did not want to waste the money she spent on it.

Dawn took off her skirt herself, showing off her body since she had not bothered to put on any kind of underwear. She left her heels and hoes on because she knew there was something sexy about them for guys. She did a twirl for Ash, so he could get a full view of her body. She giggled after she was done, and Ash turned her around pushing her towards the wall.

Dawn was a shorter than Ash, but her heels lifted her up to where he could enter her standing. Her feet were a couple feet away from the wall, and her outstretched arms rested against it. She leaned forward slightly, sticking her butt out just a little bit for him. Ash stood behind her, entering his dick into her awaiting pussy.

Ash’s mouth dropped open in pure pleasure as his cock was clamped down on. He had focused on his training abilities so heavily that he had not been with a woman in ages. He had practically forgotten what it was like to have sex. It was like having his first time over again, only this time he knew very well what he was doing and how to do it.

He penetrated deeper inside of Dawn until he thought that it was enough, and he pulled back just a little bit, so he could push his way back to the same point. He was starting off slow, letting Dawn shake her hips back against him. They found a rhythm quickly, and they were able to perform their physical tasks with little to no mental awareness.

Ash stayed in that rhythm for a little, but once he was confident that Dawn was ready for more, he gave her more. His thrusts became a little deeper, a little faster, and a lot harder. Dawn ceased her movement, staying steady now that Ash was beginning to take more control. She let out a relatively loud, extended moan with Ash’s consistent penetration.

Dawn bended down a little bit further to let Ash reach a little further. He capitalized on the opportunity, shoving his full cock inside of her on his next thrust. Dawn let out a little shriek when she felt him fill her up, but it was nothing that she couldn’t take. Ash began to pump into her a lot faster.

“Oh, yes!” Dawn let out in a hushed scream.

She did remember that they were in a fairly popular hotel, so screaming out her lungs would not be a good option for today. She kept her volume at a minimum, but it was impossible to stay completely silent. Ash was grunting every couple of seconds himself, but he was not very loud either, so it was likely that their privacy was safe for now.

Ash had continued to build up a head of steam, and his deep penetration was now coming in the form of powerful pushes. His large rod was just the perfect size for Dawn; she was “loose” enough that it could fit in her, but tight enough that it was still very pleasurable for Ash. Her walls held a strong grip on his throbbing cock.

Suddenly, there was a knock at the door. Dawn turned around and looked at Ash; their eyes locked, both of them wide-eyed. Ash chose to simple ignore it, and he kept thrusting away inside of Dawn. He figured that whoever it was could come by later, thinking that it was just a family member. Much to his surprise, the door could be heard opening just seconds later.

Ash pulled out of Dawn and turned to the door; he was not sure who he was expecting to see, but all he did know was that he was not expecting who it was. It was Misty, and she, too, was dressed up like a maid. She was wearing dark red heels with pumps thicker than the ones Dawn had. She had on white stockings that went past her knee, cutting off in a zig-zag pattern.

She was wearing a black skirt as well, but it was different than the one Dawn had on. She had some whit clothing on top of the skirt; it was a little bit like an apron, but not quite. It came up to her neck, ending in a collar, where she wore a red bow tie that matched her heels. She had on smaller, but otherwise identical ties, at the end of her short sleeves. Her side ponytail was tied off with another tie just like those, and she had on a little white tiara on her head.

“Are you going to keep fucking her or not?” She asked Ash, referring to Dawn.

Ash kept staring at her for a few more moments, and then looked at Dawn, who had turned her head around to see his face. He looked back and forth between the two, and after seeing them with the same smile, he confirmed that this had been planned by the two of them. It took him a minute, but he resumed his pumping inside of Dawn.

Misty merely watched at first, but she found herself getting turned on by the image of two of her friends going at it. She reached up her skirt with her right hand, rubbing her clit. She stayed out of the way of the other two, masturbating off to the side. It was not something that she did often, but it was not something she was a stranger to either.

As Misty waited for her turn, Dawn enjoyed hers. Ash had already gotten an orgasm out of her before they had been briefly interrupted, and that was about all she asked for out of a man. Unfortunately, not all of her previous lovers were able to provide that for her. They would be in and out of her within three minutes.

“Oh, Ash!” She moaned dreamily

Ash had managed to surpass every guy that she had been with in a multitude of ways. His girth was remarkable, his stamina was incredible, and his performance was admirable. She loved the way that each thrust he made threw her into the wall, so she could bounce back, only to be forced forward again. Unfortunately, all paradise is short lived.

She felt Ash climax inside her, causing her to release her juices as well. Ash pulled out as both of them panted. Seeing that they had finished, Misty pulled her hand away from her vagina and approached Ash. He was visibly tired, and his cock had lost a little bit of its zeal. She decided that she should go to work while he took a break.

Ash leaned his back against the wall while Misty dropped down onto her knees. She squeezed it with her hand first, gripping it tightly as she jerked him off. After her brief rubbing, she opened up her mouth and took him in. She sucked on his meat in an effort to get him excited again. With her experience and skill, she had plenty of confidence in herself.

Her tongue danced around his manhood, lightly licking all over his shaft. Ash started grunting in approval as he received his second fantastic blowjob of the day. Misty craned her eyes up, but kept performing her oral operation. Her beautiful, cerulean blue eyes locked into Ash’s brown orbs. Ash shivered a little when he looked down at her.

She was so cute and innocent, yet so dirty. Her adorable outfit coupled with the innocent gaze she gave him was a major turn on to Ash. Not to anyone’s surprise, Ash’s penis was once again a full erection. Misty could have stopped here, but she wanted to show off for him a little bit. She brought her head to the base of his cock with ease.

She only gave a small gurgle as she stuffed his entire dick into her mouth and throat. She held her head there, proving that she was the real deal. She could have held it there forever, but pulled back and resumed her bobbing. Her angelic tongue continued to pleasure Ash immensely. His cock was starting to throb once more.

Not wanting to make him finish before she even got what she wanted, Misty removed his cock from her mouth. She stood up, waiting for Ash to pick out their position. She was going to let him be in charge. She gave him a cute smile, and Ash got a little caught up staring at her again. He could hardly wait.

He threw Misty onto the bed, landing her on her backside. Her butt was near the edge of the bed, and her legs hung off. Ash separated her legs, stepping between them and throwing them over her shoulders. He folded the bottom half of her skirt up to her stomach; this way he could nail her while she still wore the outfit he liked so much.

He pushed his dick inside of her, watching her facial expressions in the process. Like a lot of women, she made some unusual faces in her intense physical joy. For some reason Ash did not find them repulsive, but rather, cute. He entered her inch by inch, waiting to see if she would give him a red light at a certain point.

Her face did appear to cringe a little once his whole member was jammed inside of her, but she did not look like she was in much pain, nor did she tell me that it was too much. Just to play it safe, Ash started by pulling out and pushing in slowly again, going just a tad bit faster this time though. He repeated the act a handful of times, picking up speed each time.

Misty was letting out growls as Ash filled her up. Ash heard her cry, which served as a sign to do whatever he liked. Suddenly, without any warning, Ash exploded into a much higher level. He had ceased the modestly increasing trend, and started to swiftly plunge his cock in and out of her. His move caught Misty completely off guard.

“OH GOD!” She yelled loudly.

Dawn, who had been resting while Misty had her fun with Ash, stepped in when she heard Misty scream. She had to keep her from being too loud, so she scooted behind her, and hovered above her face. When discussing the plans earlier, Dawn had floated around the idea of a little girl on girl action, and there had been no rejections, so she felt comfortable doing it.

Misty’s shrills were cut off once her mouth became attached to Dawn’s body. She tentatively stuck her tongue inside of her entrance. She was not completely confident in the idea, but there was no backing down, so she went for it. Being a woman herself, she understood a lot about the anatomy of a vagina, and which areas to give attention to.

Dawn quickly saw a backfire to her plan. Sure, she had managed to shut Misty up for the most part, but now she had to stay quiet herself. She had managed to keep it down when Ash was fucking her, so she told herself that she could do the same now that Misty was eating her out. However, it was tough, because Misty was lapping away at some very sensitive places.

“Mhmmm!” She bit her lip to aid her in her struggle.

Ash did not slow his pace down at all, but he slowed it down mentally. His brain was flabbergasted at the image in front of him. He was banging a dressed up Misty, and while she laid back taking his cock, she gave cunnilingus to a mostly undressed Dawn. He would have spent all of his new found fortune to have a video of the scene for himself.

Despite his mind being fascinated and captivated, his body had managed to stay on task. He had kept the beat going with his thrusting. He could faintly hear Misty letting out moans and light screams into Dawn’s pussy. When he glanced up at Dawn’s face, he saw her eyes closed and her mouth dropped open. He figured that meant that Misty was doing a good job.

His assumption was correct; Misty was touching all the right places. It did not take her very long to work Dawn into another orgasm. She cupped her mouth as she released a yell into her hands. Her body was trembling a little bit after her third orgasm, and after exclaiming that she could not take any more, she rolled away from Misty, who had reached an orgasm herself, thanks to Ash.

Wanting a change, Ash scooped Misty off of the bed. He brought her in close, running his hands along her slim body. Before he could get caught up in that, he twirled her around and shoved her right back. Her long legs stood tall, but her lower body dipped down, leaning over the bed. Ash now stuck his dick in her from behind, but before he could get started, another knock was sounded.

Ash was just as scared this time as he had been when the door sounded and he was with Dawn. A room card could be heard sliding in, an access allowing click was made, and the door opened. This time, it was May who walked through the door, and she had the sluttiest outfit of all on. Her skirt was see through from the midriff on down.

There was extra cotton up top, giving her bosom half coverage, but her stomach was visible through the black mesh, and her midnight black underwear could be seen as well. The translucent material did not even make it past her hips, showing off her long, curvy legs. She was holding a white-feather duster to complete her French Maid costume.

“Oh, don’t mind me.” She told Ash.

Ash could not make up his mind regarding who to look at. He had three great choices to pick from, and none of them could be considered a wrong answer. He focused on Misty for now, since she was the one that he was screwing. He resumed the thrusting that had halted, immediately picking up where he had left off in the previous position.

Misty could not help but to shriek in enjoyment again as Ash pounded her from behind. This time it was May who had to problem solve. She walked over to Misty, grabbed the back of her head, and pushed her face into the mattress of the bed. Her legs were still straight and extended, so her back was forced to arch itself greatly in order for her head to reach the bed.

In order to hold her head down, May had to bend over herself. The tiny skirt that she was wearing scooted up just a little bit, but that was all that was needed. Ash practically had a full view of her ass because her g-string underwear covered next to nothing. Ash now officially considered himself a lucky man.

Changing her mind from her initial plan, May crawled onto the bed, pulling her top down. Getting onto her knees, she picked Misty’s face up and shoved it into her rack. It still did the trick as far as keeping her quiet, and it put her face in a place that plenty of guys would be jealous of.

Ash was blown away by the size of May’s breasts. You could have combined the sizes of Misty’s and Dawn’s and they still would have fallen short of May’s. He would have been jealous of Misty, but he was in great position too. He continued to slam his package inside of Misty’s entrance, making her moan loudly into May’s pillows.

He was drilling her with all of his might, ramming his cock in with as much power as he had left in him. He lost control of his body; his hips went absolutely wild, pumping back and forth. He felt Misty orgasm again, clamping down on his cock incredibly tight in the process. This served as the last straw, and Ash spilled his seed inside of her right afterwards.

After he was confident that every last drop had escaped, Ash pulled himself out of Misty. Misty rolled over onto her back, panting heavily, mouth opened into the widest smile she’d ever had. She seemed to be reliving the heaven she had just been through in her head. Ash sat down on the bed; he was spent.

Seeing how tired he was, May stepped up to the plate. She pulled her top back over her breasts, covering them once more. She crawled on top of Ash and started to grind on him. She tried to show all of her body off, giving him quick peaks at her breasts, shaking her hips, and rubbing her core up against his.

After giving him a quick dance, she pulled her tits out once more. Instead of covering the right back up, she brought them down to Ash’s cock, smothering it with them. She squeezed them together tight, rubbing them all along his shaft. Her plan worked to perfection. Almost against his will, Ash’s cock had hardened for the third time.

He reached and petted her marvelous boobs, while she continued to slide them along his pole. They were so soft to touch, but they also made for a firm resting place. If they were any bigger, they would probably cross the line into the “too big” zone. Not all guys have one, but Ash did. May’s boobs, however, were the ideal size in his book.

Now that she thought Ash was fully ready, May pulled her knockers away from him. She took off the skirt, leaving only her black panties that she slipped off smoothly. She knew that Ash was still worn out, so she hopped on him cowgirl style. She lowered herself onto his meat, not stopping until all of him was inside of her.

She started out like someone would the first time they rode a horse. She kept if fairly slow and tried to move as smoothly as possible. She found a pace she liked rather quickly, and she kept it right there. Ash filled her better than any man she could recall, and she was not going to let his size go to waste.

Now that May had settled in on a steady tempo, Misty and Dawn got involved. They crept over to opposite sides of May, each of them taking one of her breasts in their mouth. May had had guys lick on her breasts before, but they only had one mouth of course. It was new to have a mouth on both of them at the same time.

“Oh my GOD!” She moaned.

Her nipples were very sensitive, so when both of them got sucked on, coupled with riding a big dick, she was in a level of ineffable bliss. Dawn began to finger herself, feeling that she had had enough time off to get another good orgasm out. She played with herself with her hand while she continued lick and suck on May’s left breast.

May inadvertently slowed down the speed of her hip movements due to the pleasure given to her by Dawn and Misty. All three of them had insisted that they had never done anything with a girl when they were planning out the event, but May started to doubt the veracity of that statement now. They were a little too good to be beginners in her minds.

All of the attention that she was receiving trumped any of her past experiences. This time would stand alone in her mind, partly because she had never tried even a threesome, much less a foursome. Her voice continued to raise up in volume, so Dawn again had to stop it. She retracted the two fingers that she had used to penetrate herself, and she stuck inside of May’s mouth.

“Shhhh… that’s better.” Dawn said as she lifted her mouth up momentarily.

May was forced to suck on Dawn’s wet fingers. Her fingers were lathered in her pre cum, giving them a strange taste. It was tangy, tart, yet a little bit sweet. May thought it tasted a little bit metallic, which sounded strange to her, but it was what came to mind. She did not find it enjoyable, but she did not have much of a choice.

Her brain was having a tough time processing everything that was going on. With four parts of her body involved in a sexual activity, it was as erotic a scene as she could imagine. It was no surprise that she orgasmed after only a couple minutes. Her yelp was muffled because Dawn’s index and middle finger were sitting on her tongue.

She pulled Dawn’s fingers out of her mouth, and she ceased her bouncing movements on Ash. She thought that since she had gotten her orgasm that they were all finished. Misty and Dawn stopped sucking on her tits as they realized that May appeared to be stopping on them. A strange silence fell, but Ash broke it.

“You don’t think that’s it, do you?” He seemed to be talking to May.

He flipped May off of him, and then pushed her onto all fours. Performing all of his maneuvers quickly, he got on his knees behind her, entering her doggy style. May was surprised that he thought he had the energy to take the lead role in another round, but she was hardly complaining when he stuck his member back inside of her.

He thrusted roughly into her, shaking not only her body, but also the bed. His powerful movements stuck May right back onto cloud nine. He filled her entire body with pleasure, simply be sticking his dick into her. May thought it was just magical. She started to moan loudly again, and this time Misty thought of something.

She picked up the skimpy underwear that had belonged to her, and she stuck that in her mouth. May once again tasted the unique taste of a women, but this time it was from herself. It was a little disgusting to her, but something about being forced to do it made it hot for her. Her screams were muted by her underwear.

“Mhgh!” Was the sound that transmitted through the fabric.

Misty held the underwear in her mouth, providing Dawn with an idea. She grabbed two strands of May’s hair, one on each side, and she pulled back on it. This forced May to arch her back almost as much as Misty had to when she was getting her turn. Because of her body position, Ash was able to reach even deeper areas of her vagina.

Her muffled screams practically double as Ash repeatedly slammed his thick cock into new depths. Nobody had ever reached that far inside of her before. Ash’s cock was getting compressed tightly by her enclosing walls. He tried to think of something else to keep himself from finishing too early.

Unfortunately, it was hard to think of something not sexual when he had three beautiful women on the same bed as himself. He loved watching May being forced to take it. He knew that she was really not against her will, but with Misty, Dawn, and him controlling her body, it could almost seem like she was.

There were three prominent noises sounding throughout the room. The most present was the thwacking sound that was created with each entrance that Ash made inside May. With his current pace, there was one every second. The second sound was also creating by skin on skin, and it was the sound of her boobs. They were flinging around wildly, smacking all over her own chest.

That sound was overshadowed by the grumbled screaming that May was making. She had already squirted a couple of times since changing positions. She was getting tired, so she could only imagine how Ash was holding. He must have swapped stamina’s with a marathon runner because he just kept finding a way to keep going.

Ironically, as this comparison occurred to May, Ash finally ran out of energy. Surprisingly, another shot of sperm managed to come out of him, even though he had already spewed out two. This time when he pulled out, he was completely and utterly exhausted. He flopped back onto the bed, breathing softly. The other girls let go of May, and her body collapsed down onto the bed as well.

Even though he had already taken one for the day, a nap was what sounded pretty good to Ash now that he had drained his body once more. Misty, May, and Dawn curled up next to him on the bed, ready to get some sleep themselves. Just as Ash was about to shut his eyes, there was a knock on the door. Ash looked at the girls, assuming that they were behind this one too.

But instead of devious smiles, he saw three panic-stricken girls staring at each other.


End file.
